One-pot synthesis of substituted-amino triazole-glycosides

Article abstract of DOI:10.1016/j.carres.2019.107780

This work combined three classes of compounds in the same molecule “amino triazole-glycoside” and developed a convenient method for the synthesis of this type of compound via a one-pot two step reaction. Alkylation of amine derivatives with propargyl bromide to give propargylamine was performed in the first step subsequently followed by a ‘click’ reaction with various β-azido-glycosides in the presence of CuI in aqueous solution to provide β-amino triazole-glycosides. Thirty-two examples of glycosides were obtained in moderate to good yield using this one-pot procedure.

Full text of DOI:10.1016/j.carres.2019.107780

Journal Pre-proof
One-pot synthesis of substituted-amino triazole-glycosides
Warapond Sutcharitruk, Uthaiwan Sirion, Rungnapha Saeeng
PII:
S0008-6215(19)30316-7
DOI:
https://doi.org/10.1016/j.carres.2019.107780
CAR 107780
Reference:
To appear in: Carbohydrate Research
Received Date: 22 May 2019
Revised Date: 15 August 2019
Accepted Date: 16 August 2019
Please cite this article as: W. Sutcharitruk, U. Sirion, R. Saeeng, One-pot synthesis of substituted-amino
triazole-glycosides, Carbohydrate Research (2019), doi: https://doi.org/10.1016/j.carres.2019.107780.
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One-pot synthesis of substituted-amino triazole-glycosides
Warapond Sutcharitruk, Uthaiwan Sirion, Rungnapha Saeeng*
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Graphic Abstract
K2CO3, KI
Br
NHR1R2
N
N
O
or DIPEA, TBAI
+
NR1R2
N
(AcO)
O
CuI, H2O
N3
(AcO)
32 examples
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Highlights
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►
An efficient one-pot, two step reaction was developed for synthesis of amino triazole-
glycosides.
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►
Thirty-two examples of new amino triazole-glycoside derivatives were synthesized in
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moderate to good yields.
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One-pot synthesis of substituted-amino triazole-glycosides
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Warapond Sutcharitruk, Uthaiwan Sirion, Rungnapha Saeeng*
Department of Chemistry and Center for Innovation in Chemistry, Faculty of Science,
Burapha University, Saensook, Chonburi 20131, Thailand
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*Corresponding Author Department of Chemistry and Center for Innovation in Chemistry,
Faculty of Science, Burapha University, Saensook, Chonburi 20131, Thailand.
E-mail: rungnaph@buu.ac.th, Fax: +66-3-839-3494; Tel: +66-81-656-7524
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Abstract
This work combined three classes of compounds in the same molecule “amino triazole-
glycoside” and developed a convenient method for the synthesis of this type of compound via
a one-pot two step reaction. Alkylation of amine derivatives with propargyl bromide to give
propargylamine was performed in the first step subsequently followed by a ‘click’ reaction
with various β-azido-glycosides in the presence of CuI in aqueous solution to provide β-
amino triazole-glycosides. Thirty-two examples of glycosides were obtained in moderate to
good yield using this one-pot procedure.
Key words: amino triazole-glycoside; one pot; N-alkylation; click reaction
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1. Introduction
Glycosides exist in natural product structures with roles in a broad range of
biological processes [1-5]. Their utility was recognized as chiral pool substances for the
synthesis of selective enantiomeric glycosides [6-9]. Amino glycosides have been the focus
of much research in recent years due to their interesting biological pharmacophore unit. β-
Amino glycoside-containing complex natural compounds are found in nature as important
biological substances [10-11] such as isepamicin [12], plazomicin [12-13] and gentamicin C2
(Figure 1) [14-16].
HO
NH
O
HO
HO
OH
CH3
NH2
NH2
O
O
O
H2N
HO
OH
NH2
H3C
H3C
HN
H3C
H2N
HO
H
O
O
OH
O
HN
H3C
HO
HO
N
HO
HO
O
O
O
O
O
NH2
NH2
H2N
O
HO
NH2
HN
HO
H3CHN
CH3
H2N
O
OH
Gentamicin (GEN)
Plazomicin (PLZ)
Isepamicin (ISP)
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Figure 1. Structure of bioactive compounds containing amino glycosides
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Glycosides can also be covalently linked to other functional groups including
heterocycle triazoles for therapeutic applications [17-20]. This quality arises from the
stability of triazole rings toward metabolic degradation and the high dipole moment and
strong hydrogen bonding interactions which improve solubility in water. The triazole unit
was also recognized as bioisostere of the amide functionality [21]. This has led to much
research on the synthesis of triazole containing compounds which possess a wide range of
biological activities [22-25]. The popular utilization of 1,2,3-triazoles is largely driven by
their facile synthesis via click reactions [26] as a powerful, highly reliable synthesis of useful
compounds. In this study, we describe new strategies in glycosylation reactions to combine
the biologically interesting substances, aminoglycoside and triazole that are of growing
importance in the synthesis of bioactive glycosides. Those are currently available still have
problems associated with functionalization of glycosides causing them to lag behind other
functional groups. Careful optimization of all parameters including the promoter or catalyst,
protecting group and glycosylation conditions is crucial to improve yields and high
stereoselectivity. Hence, new efficient glycoside methodologies for the glycosylation
reactions with the intrinsic diversity of carbohydrates still attract great interest [27].
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4
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Therefore, in this work, we developed a synthetic method for β-amino triazole-
glycosides via a rapid one-pot synthesis from the click reaction of β-azido glycoside and
propargyl amine generated in-situ by N-alkylation of readily available amine derivatives and
propargylbromide (Scheme 1).
O
N
N
N3
N-alkylation
(AcO)
O
Br
NHR R
+
1
2
NR1R2
NR1R2
N
(AcO)
6
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Scheme 1. One pot synthesis of amino triazole-glycosides
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2. Results and discussion
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Table 1. Screening of the reaction conditions
H
N
OAc
O
OAc
O
N
N
conditions
AcO
AcO
AcO
AcO
+
2a
3a
N
N
N3
OAc
click reaction
OAc
Br
1a
4a
12
Amine
(equiv)
2.0
Additive
(equiv)
-
Yield
Entry
Base (equiv)
Solvent (1:2) Time (h)
(%)
0
1
2
3
4
5
Et3N (2.0)
Et3N (1.0)
CH2Cl2:H2O
CH2Cl2:H2O
CH2Cl2:H2O
CH2Cl2:H2O
CH3CN:H2O
24
10
24
24
4
2.0
-
52
54
74
95
2.0
DIPEA (1.0)
DIPEA (1.0)
K2CO3 (1.0)
TBAI (0.2)
TBAI (0.2)
KI (0.2)
1.2
1.2
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a Reaction conditions in entries 1-4 : 1a (0.27 mmol), 2a(1.2 equiv), 3a (2 equiv) for 24 h.
b Reaction conditions in entry 5 : 1a (0.27 mmol), 2a (1.2 equiv), 3a (2 equiv) at 70 oC.
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A one-pot procedure using the three components amine, propargyl halide and azide
via a two-step click reaction and N-alkylation has been reported by Liang and coworkers
[28]. This method employed triethylamine and CuI in water, however, the procedure was not
applicable for azidoglycoside compounds. We observed low yields of products and complex
side products with many glycoside examples. Therefore, we developed a new procedure
using DIPEA or potassium carbonate and additives as given in Table 1 in our procedure for
glycoside synthesis. Initially, we investigated the three component one-pot N-alkylation click
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reaction between glycosylazide, N-methylaniline and propargyl bromide as the model
reaction for screening of optimal conditions as shown in Table 1. The reaction was first
conducted in a 2:1 mixture of water and dichloromethane using CuI in H2O as catalyst in the
click reaction. No target product was observed when the reaction was carried out for 24 h
with triethylamine (2 equiv.) as the base (Entry 1), probably due to the decomposition of
product during the long reaction time. With these conditions, we observed side products from
the excess trimethylamine reacting with propargylbromide. Decreasing the amount of
triethylamine to 1 equiv. and shortening the reaction time to 10 h, glycoside 4a was obtained
in 52%yield (Entry 2). To optimize the reaction conditions, DIPEA was employed as a base
with TBAI as an additive in the N-alkylation step giving a product yield of 54%. Decreasing
amount of N-methylaniline to 1.2 equiv. gave a product yield of 74%. Further optimization
with different bases, additives and solvents, found K2CO3 to be the most effective base in the
presence of KI as an additive and a mixture of H2O and CH3CN as the solvent, offering
glycoside 4a in excellent yield (95%).
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Table 2. One-pot synthesis of acetylated 1-[β-D-glucosyl]-4-(amino)-triazoles from
acetylated β-D-glucosyl azides 1a
OAc
O
NHR1R2
OAc
O
N
N
N
1)
i or ii
AcO
AcO
AcO
AcO
+
2a
Br
3a
NHR1R2
4a-4l
N3
OAc
OAc
1a
2) CuI (0.1 equiv),
H2O
OAc
O
OAc
O
OAc
O
N
N
N
N
N
N
H
AcO
AcO
AcO
AcO
AcO
AcO
N
N
N
N
N
N
OAc
OAc
OAc
4a[a
4ba
(95%)
4ca (74%)
(87%)
OAc
O
OAc
O
OAc
O
N
N
N
N
N
N
N
H
N
H
H
AcO
AcO
AcO
AcO
AcO
AcO
F
N
N
N
N
OAc
OAc
OAc
4da
4fa
Br
(78%)
4ea
F
(73%)
(78%)
OAc
O
OAc
O
OAc
O
N
N
N
N
N
H
N
N
AcO
AcO
AcO
AcO
AcO
AcO
N
N
N
N
N
OAc
OAc
OAc
4ga (58%)
4ha
4ia (48%)
(58%)
OAc
O
OAc
O
OAc
O
O
N
N
N
N
N
N
N
H
AcO
AcO
AcO
AcO
AcO
AcO
N
N
N
N
N
OAc
OAc
OAc
4ja (51%)
b
a
(54%)b, (32%)a
4l
4k
(96%) , (50%)
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5

a
1
2
3
4
Reaction conditions : 1a(0.27 mmol), 2a (1.2 equiv), 3a (2.0 equiv), K2CO3 (1.0 equiv), KI (1.0 equiv) at 70
oC
b
Reaction conditions : 1a (0.27 mmol), 2a (1.2 equiv), 3a (2.0 equiv),DIPEA (1.0 equiv), TBAI (0.2nequiv) at
room temperature.
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Under optimized conditions, a variety of amines such as substituted aromatic amines,
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aliphatic and heterocyclic amines were used to perform the N-alkylation with propargyl
bromide followed by a click reaction in one pot (Table 2).
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Acetylated β-D-glucosyl azides reacted smoothly in the presence of CuI in H2O with
propargyl amine derived from 2o-substituted anilines to furnish glycoside 4a and 4b in
excellent yields while 1o-substituted anilines gave good yields of products 4c-4f.
Furthermore, 1o- and 2o-aliphatic amines yielded products 4h-4j in a moderate yield,
presumably due to steric hindrance and weak nucleophilicity. Functional groups, such as two
olefinic groups in 4h, was also successful with these reaction conditions. Heterocyclic amines
such as pyrrolidine and morpholine were also examined in the one-pot reaction system,
however, the process using K2CO3 and KI was not effective. A significant increase in yield
was observed when 1.0 equiv of DIPEA and 0.2 equiv of TBAI were employed at room
temperature improving the yield to 54 and 96 % respectively.
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Table 3. One-pot synthesis of acetylated 1-[β-D-galactosyl]-4-(amino)-triazoles from
acetylated β-D-galactosyl azides 5a
AcO
AcO
AcO
AcO
OAc
O
OAc
O
NHR1R2
N
N
N
1)
i or ii
+
2a
NHR1R2
6a-6i
N3
2) CuI (0.1 equiv),
H2O
OAc
OAc
5a
Br
3a
AcO
AcO
OAc
O
AcO
AcO
OAc
O
AcO
AcO
N
N
OAc
O
N
N
N
N
N
H
N
H
N
N
N
N
F
OAc
OAc
OAc
6aa (95%)
6ba (48%)
6ca (75%)
AcO
AcO
OAc
O
AcO
AcO
OAc
O
AcO
AcO
OAc
O
N
N
N
N
H
N
N
N
H
N
N
N
N
N
OAc
OAc
OAc
6da (48%)
F
6ea (71%)
Br
6fa (75%)
AcO
AcO
OAc
O
AcO
AcO
OAc
O
AcO
AcO
N
OAc
O
N
O
N
N
N
N
N
N
N
N
N
N
OAc
OAc
OAc
6ga (68%)
6hb (54%)
6ib (96%)
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a Reaction conditions : 1a(0.27 mmol), 2a (1.2 equiv), 3a (2.0 equiv), K2CO3 (1.0 equiv), KI (1.0 equiv) at 70 oC
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b Reaction conditions : 1a (0.27 mmol), 2a (1.2 equiv), 3a (2.0 equiv),DIPEA (1.0 equiv), TBAI (0.2 equiv) at
room temperature.
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5
6
7
8
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The scope of the one-pot protocol was extended to acetylated β-D-galactosyl
azides which also provided efficient access to acetylated 1-[β-D-galactosyl]-4-(amino)-
triazoles (Table 3). Acetylated β-D-galactosyl azides reacted smoothly with propargyl amine
derived from substituted amines to give glycosides 6a-6i in moderate to excellent yields.
Notably, aliphatic amines underwent the N-alkylation click reaction with acetylated β-D-
galactosyl azides 5a and propargyl bromide 3a, affording products 6f and 6g in good yields.
Heterocyclic amines gave 6h and 6i in good to excellent yields using DIPEA/TBAI.
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Table 4 Substrate scope of the acetylated β-D-glycosyl azide derivatives
NHR1R2
N
N
N
1)
i or ii
O
O
+
2a
3a
NHR1R2
N3
(AcO)
(AcO)
2) CuI (0.1 equiv),
H2O
Br
10a-10d or 11a-11b or 12a-12b
7a, 8a, 9a
AcO
O
AcO
O
O
AcO
AcO
AcO
or
N3
N3
or
N3
AcO
OAc
7a
OAc
8a
OAc
9a
N
N
N
N
N
N
N
N
O
O
O
AcO
AcO
AcO
AcO
AcO
AcO
N
N
N
N
OAc
OAc
OAc
10ba (76%)
10aa (88%)
10ca
(76%)
AcO
AcO
AcO
AcO
O
N
N
N
N
N
N
N
N
N
O
O
AcO
AcO
O
N
N
N
OAc
OAc
OAc
10db (48%)
11aa (55%)
11ba (51%)
O
AcO
O
N
AcO
N
N
N
O
AcO
AcO
N
N
N
N
OAc
OAc
12bb
12aa (51%)
(72%)
11
12
a
13
14
15
16
Reaction conditions : 1a(0.27 mmol), 2a (1.2 equiv), 3a (2.0equiv), K2CO3 (1.0 equiv), KI (1.0 equiv) at 70 oC
b Reaction conditions : 1a (0.27 mmol), 2a (1.2 equiv), 3a (2.0equiv),DIPEA (1.0 equiv), TBAI (0.2 equiv) at
room temperature.
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Additionally, the synthetic utility of our one-pot three component reaction was
investigated with acetylated β-D-xylosyl azides 7a, acetylated β-L-arabinosyl azides 8a and
acetylated β-D-arabinosyl azides 9a (Table 4). All azido-sugar analogues reacted smoothly
with in situ generated-propargylamines to give glycoside products in moderate to good
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4
5
6
7
8
9
yields. Acetylated 1-[β-D-xylosyl]-4-(amino)-triazoles 10a-10c were manufactured in high
yields from 7a while morpholine gave a moderate yield of 10d.
Acetylated β-L-arabinosyl azide 8a was examined as substrate for the synthesis of
amino triazolearabinosides. Aromatic amines and aliphatic amine derivatives, gave 11a and
11b in 55 and 51% yields respectively. Subsequently, acetylated β-D-arabinosyl azides (9a)
with aromatic and heterocyclic amines resulted in structural derivatives 12a and 12b in
excellent yields.
Table 5. One-pot synthesis of amino bistriazole-glycoside
OAc
N
O
N
R
N
AcO
AcO
NH2R
OAc
O
N
1) DIPEA, TBAI, CH2Cl2
OAc
AcO
AcO
2a
N3
OAc
1a
2) CuI (0.1 equiv),
H2O
AcO
O
N
13a-13c
Br
N N
OAc
OAc
3a
AcO
OMe
OMe
OMe
OAc
O
OAc
O
N
N
N
N
N
AcO
AcO
AcO
AcO
N
N
OAc
N
N
OAc
13bc (32%)
13ac (40%)
AcO
O
N
AcO
N N
O
N N
OAc
OAc
OAc
OAc
AcO
Br
AcO
OAc
O
N
N
AcO
AcO
N
N
N
OAc
13cc
AcO
(32%)
O
N N
OAc
OAc
AcO
10
11
12
c Reaction conditions : 1a (0.27 mmol, 1.0 equiv), 2a (0.5 equiv), 3a (2.2 equiv),DIPEA (1.0 equiv), TBAI
(0.2equiv) at room temperature
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15
16
17
18
19
Application of the one-pot three-component reaction for the synthesis of amino-
bistriazoleglycosides was explored using substituted aromatic amines in the presence of
DIPEA (1.0 equiv), propargyl bromide (2.2 equiv) and CH2Cl2 as the solvent (Table 5).
Under these conditions, the β-amino-bistriazole-glycoside derivatives 13a, 13b and 13c were
obtained initially in moderate yields due to steric hindrance, however, this demonstrates the
generality of this one-pot reaction.
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3. Conclusions
2
3
We have developed an efficient rapid procedure for the synthesis of novel β-amino
triazole glycoside derivatives with a three-component one-pot protocol. A variety of amines
reacted with propargylbromide in an N-alkylation step using DIPEA/TBAI or K2CO3/KI
followed by a click reaction with various acetylated β-D-glycosyl azides in the presence of
CuI in water. By executing all of the reaction steps in a single pot and purifying only at the
final stage, this procedure showed considerable advantages in terms of mild reaction
conditions, simplicity and good product yields. This methodology is a good general protocol
for the syntheses of acetylated 1-[β-D-glycosyl]-4-(amino)-triazoles, offering a wide variety
of applications.
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4. Experimental Section
General
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Experimental Procedures: All chemicals were purchased from commercial sources and used
without further purification. Proton NMR spectra were recorded on a Bruker Avance (400
MHz). All spectra were measured in CDCl3 solvent and chemical shifts are reported as δ
values in parts per million (ppm) relative to tetramethylsilane (δ 0.00) or CDCl3 (δ 7.26) as
internal standard. Data are reported as follows; chemical shift (multiplicity, integrate intensity
or assignment, coupling constants in Hz, assignment). Carbon NMR spectra were recorded on
a BRUKER AVANC (100 MHz). All spectra were measured in CDCl3 solvent and chemical
shifts are reported as δ values in parts per million (ppm) relative to CDCl3 (δ 77.0) as internal
standard. High-resolution mass spectra (HRMS) data were obtained with a Finnigan MAT 95
at Mahidol University. Infrared spectra were determined on a PERKIN ELMER FT/IR-2000S
spectrophotometer and are reported in wavenumber (cm−1). Analytical thin-layer
chromatrography (TLC) was conducted on precoated TLC plates; silica gel 60F-254 [E.
Merck, Darmstadt, Germany]. Silica gel columns for open-column chromatrography utilized
silica gel 60 PF254 [E. Merck, Darmstadt, Germany]. Melting points were measured using a
melting point apparatus (Griffin) and are uncorrected.
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General Procedure (A): The solution of amine (0.32 mmol) in acetronitrile 1 mL was added
K2CO3 (37.3 mg, 0.27 mmol) and potassium iodine (44.8 mg, 0.27 mmol). The resulting
solution was stirred at room temperature for 10 min. Propargyl bromide (0.04 mL, 0.54
mmol) was then added and the reaction was stirred at 70oC temperature until TLC showed the
complete conversion (3 h-24 h). Then the reaction mixture was added H2O 2 mL and glycosyl
azide (100 mg, 0.27 mmol) and CuI (5.7 mg, 0.03 mmol). The reaction mixture was
continuously stirred at room temperature until completion of reaction as indicated by
appearance of a new spot on the TLC plates. The reaction mixture was diluted with CH2Cl2
and poured into EDTA solution. The mixture was stirred for 5 min. then the reaction mixture
was extracted with CH2Cl2. The organic layers were dried over anhydrous Na2SO4 and
concentrated under reduced pressure to afford the crude compound which was further
purified by column chromatography.
3
4
5
6
7
8
9
10
11
12
13
14
15
16
1-(2,3,4,6-Tetra-O-acetyl-β-D-glucopyranosyl)-4-(methylphenylamino)-1,2,3-triazole
(4a): General procedure A was followed, starting with N-methylaniline (0.03 mL, 0.32
mmol). The reaction mixture was stirred for 3 h and was purified by column chromatography
(n-hexane/EtOAc 7:3) provided the product as a white solid in 95% yield (139.4 mg); Rf =
17
0.10 (n-hexane/EtOAc 7:3); [α] ꢀꢁ-25.4 (c 0.5, CHCl3 ); mp = 167-168 °C; IR (film) 2954,
ꢂ
18
19
20
21
22
23
24
25
26
27
28
29
30
1755, 1600, 1507, 1369, 1226, 1039, 751, 693 cm-1; 1H NMR (400 MHz, CDCl3) δ 7.53 (s,
1H, H-triazole), 7.24 (t, J = 8.0 Hz, 2H, H-Ar), 6.79 (d, J = 8.3 Hz, 2H, H-Ar), 6.75 (t, J = 7.2
Hz, 1H, H-Ar), 5.81 (1d, J = 8.0 Hz, 1H, H-1), 5.41-5.33 (m, 2H, H-2, H-4), 5.23-5.16 (m,
1H, H-3), 4.63 (s, 2H, H-3′), 4.26 (dd, J = 12.0, 4.0 Hz, 1H, H-6a), 4.12 (d, J = 12.0 Hz, 1H,
H-6b), 3.96 (dd, J = 9.4, 3.8 Hz, 1H, H-5), 3.00 (s, 3H, H-NCH3), 2.06 (s, 3H, OAc), 2.05 (s,
3H, OAc), 2.00 (s, 3H, OAc), 1.79 (s, 3H, OAc); 13C NMR (100 MHz, CDCl3) 170.48,
169.88, 169.29, 168.74, 148.97, 146.29, 129.25 (2C), 119.96, 117.32, 113.05 (2C), 85.67,
75.12, 72.61, 70.15, 67.69, 61.48, 48.59, 38.51, 20.66, 20.50, 20.46, 20.00; HRMS (ESI) m/z
calcd. for C24H30N4O9Na (M+Na)+ 541.1910, found 541.1909.
1-(2,3,4,6-Tetra-O-acetyl-β-D-glucopyranosyl)-4-(butyl(phenyl)amino)-1,2,3-triazole
(4b): General procedure A was followed, starting with N-n-butylaniline (0.05 mL, 0.32
mmol). The reaction mixture was stirred for 3 h and was purified by column chromatography
(n-hexane/EtOAc 3:2) provided the product as a brown solid in 87% yield (140.5 mg); Rf =
31
0.17 (n-hexane/EtOAc 3:2); [α] ꢀꢁ -24.0 (c 0.5, CHCl3 ); mp = 103-105 °C; IR (film) 2958,
ꢂ
1
32
33
1756, 1599, 1506, 1369, 1226, 1039, 750, 694 cm-1; H NMR (400 MHz, CDCl3) δ 7.51 (s,
1H, H-triazole), 7.21 (t, J =7.5 Hz, 2H, H-Ar), 6.74-6.67 (m, 3H, H-Ar), 5.80 (dd, J = 6.4, 2.4
10

1
2
3
4
Hz, 1H, H-1), 5.41-5.33 (m, 2H, H-2, H-4), 5.19 (ddd, J = 9.6, 6.2, 2.8 Hz, 1H, H-3), 4.61 (s,
2H, H-3′), 4.26 (dd, J = 12.4, 4.8 Hz, 1H, H-6a), 4.12 (dd, J = 12.4, 1.5 Hz, 1H, H-6b), 3.96
(ddd, J = 10.0, 4.8, 2.0 Hz, 1H, H-5), 3.35 (t, J = 7.6 Hz, 2H, H-4′), 2.06 (s, 3H, OAc), 2.05
(s, 3H, OAc), 2.00 (s, 3H, OAc), 1.79 (s, 3H, OAc), 1.62 (quint, J = 7.4 Hz, 2H, H-5′), 1.36
13
5
6
(sext, J = 7.2 Hz, 2H, H-6′), 0.94 (t, J = 7.2 Hz, 3H, H-7′); C NMR (100 MHz, CDCl3) δ
170.44, 169.85, 169.25, 168.63, 147.89, 147.04, 129.25 (2C), 120.08, 116.58, 112.54 (2C),
85.59, 75.03, 72.62 70.08, 67.64, 61.45, 51.02, 46.64, 29.36, 20.61, 20.46, 20.42, 20.21,
19.97, 13.90; HRMS (ESI) m/z calcd for C27H37N4O10 (M+H)+ 561.2561, found 561.2573.
1-(2,3,4,6-Tetra-O-acetyl-β-D-glucopyranosyl)-4-(naphthalen-2-ylamino)-1,2,3-triazole
(4c): General procedure A was followed, starting with 1-naphthylamine (45.8 mg, 0.32
mmol). The reaction mixture was stirred for 3 h and was purified by column chromatography
(n-hexane/EtOAc 3:7) provided the product as a brown solid in 74% yield (113.3 mg); Rf =
7
8
9
10
11
12
13
0.12 (n-hexane/EtOAc 3:7); [α] ꢀꢁ -30.4 (c 0.5, CHCl3 ); mp = 159-161 °C; IR (film) 3923,
ꢂ
1
14
15
16
17
18
19
20
21
22
23
24
25
26
27
2853, 1755, 1583, 1529, 1369, 1227, 1049, 772, 736 cm-1; H NMR (400 MHz, CDCl3): δ
7.90-7.84 (m, 1H, H-Ar), 7.82-7.78 (m, 1H, H-Ar), 7.77 (s, 1H, H-triazole), 7.50-7.42 (m, J =
4.8 Hz, 2H, H- Ar-), 7.38-7.25 (m, 2H, H-Ar), 6.66 (d, J = 7.6 Hz, 1H, H-Ar), 5.86 (d, J = 9.2
Hz, 1H, H-1), 5.46-5.37 (m, 2H, H-2, H-4), 5.27-5.14 (m, 1H, H-3), 4.65 (s, 2H, H-3′), 4.28
(dd, J = 12.5, 4.8 Hz, 1H, H-6a), 4.14 (dd, J = 12.8, 1.6 Hz, 1H, H-6b), 3.98 (ddd, J = 10.0,
13
4.8, 2.0 Hz, 1H, H-5), 2.06 (s, 6H, OAc), 2.02 (s, 3H, OAc), 1.84 (s, 3H, OAc); C NMR
(100 MHz, CDCl3) δ 170.46, 169.87, 169.30, 168.88, 146.73, 142.51, 134.26, 128.63,
126.45, 125.84, 124.94, 123.60, 120.21, 119.97, 118.24, 105.03, 85.75, 75.14, 72.59, 70.24,
67.67, 61.48, 40.06, 20.64, 20.50, 20.47, 20.10; HRMS (ESI) m/z calcd for C27H30N4O9Na
(M+Na)+ 577.1910, found 577.1966.
1-(2,3,4,6-Tetra-O-acetyl-β-D-glucopyranosyl)-4-(3-fluorophenylamino)-1,2,3-triazole
(4d): General procedure A was followed, starting with 3-fluoroaniline (0.03 mL, 0.32 mmol).
The reaction mixture was stirred for 3 h and was purified by column chromatography (n-
hexane/EtOAc 3:2) provided the product as a brown solid in 78% yield (108.1 mg); Rf = 0.12
28
(n-hexane/EtOAc 3:2); [α] ꢀꢁ -23.9 (c 0.5, CHCl3 ); mp = 163-164 °C; IR (film) 3400, 2923,
ꢂ
29
30
31
32
33
1755, 1620, 1369, 1228, 1040, 764 , 684 cm-1; 1H NMR (400 MHz, CDCl3) δ 7.71 (s, 1H, H-
triazole), 7.11 (td, J = 7.8, 7.8 Hz, 1H, H-Ar), 6.47-6.39 (m, 2H, H-Ar), 6.33 (d, J = 11.2 Hz,
1H, H-Ar), 5.85 (dd, J = 6.8, 2.4 Hz, 1H, H-1), 5.45-5.37 (m, 2H, H-2, H-4), 5.22 (ddd, J =
10.0, 6.8,28 Hz, 1H, H-3), 4.44 (s, 2H, H- 3′), 4.29 (dd, J = 12.8, 4.8 Hz, 1H, H-6a), 4.14 (dd,
J = 12.8, 2.0 Hz, 1H, H-6b), 3.99 (ddd, J = 10.0, 4.8, 2.0 Hz, 1H, H-5), 2.07 (s, 3H, OAc),
11

13
1
2
2.06 (s, 3H, OAc), 2.02 (s, 3H, OAc), 1.83 (s, 3H, OAc); C NMR (100 MHz, CDCl3) δ
170.40, 169.81, 169.28, 168.82, 163.94 (d, J = 242.0 Hz, C-F), 149.12 (d, J = 10.0 Hz, Cm-F),
146.39, 130.29 (d, J = 10.0 Hz, Cm-F), 120.00, 108.94 (d, J = 2.0 Hz, Cp-F), 104.28 (d, J =
22.0 Hz, Co-F), 99.78 (d, J = 25 Hz, Co-F), 85.60, 75.01, 72.51, 70.11, 67.62, 61.44, 39.56,
20.56, 20.43, 20.39, 19.94; HRMS (ESI) m/z calcd for C23H27FN4O9Na (M+Na)+ 545.1660,
found 545.1664.
3
4
5
6
7
1-(2,3,4,6-Tetra-O-acetyl-β-D-glucopyranosyl)-4-(4-fluorophenylamino)-1,2,3-triazole
(4e): General procedure A was followed, starting with 4-fluoroaniline (0.03 mL, 0.32 mmol).
The reaction mixture was stirred for 3 h and was purified by column chromatography (n-
hexane/EtOAc 3:2) provided the product as a brown solid in 78% yield (106.1 mg); Rf = 0.10
8
9
10
11
(n-hexane/EtOAc 3:2); [α] ꢀꢁ-27.2 (c 0.5, CHCl3 ); mp = 193-194 °C; IR (film) 3391, 2923,
ꢂ
1
12
13
14
15
16
17
18
19
20
21
22
23
24
25
1755, 1514, 1369, 1224, 1040, 825cm-1; H NMR (400 MHz, CDCl3) δ 7.70 (s, 1H, H-
triazole), 6.90 (t, J = 8.4 Hz, 2H, H-Ar), 6.57-6.64 (dd, J = 8.8, 4.0 Hz, 2H, H-Ar), 5.85 (dd, J
= 6.4, 2.4 Hz, 1H, H-1), 5.44-5.36 (m, 2H, H-2, H-4), 5.22 (ddd, J = 9.7, 6.7, 2.4 Hz, 1H, H-
3), 4.42 (s, 2H, H-3′), 4.29 (dd, J = 12.5, 4.8 Hz, 1H, H-6a), 4.14 (dd, J = 12.4, 2.0 Hz, 1H,
H-6b), 3.98 (ddd, J = 10.0, 4.8, 2.0 Hz, 1H, H-5), 2.07 (s, 3H, OAc), 2.06 (s, 3H, OAc), 2.02
13
(s, 3H, OAc), 1.82 (s, 3H, OAc); C NMR (100 MHz, CDCl3) δ 170.41, 169.82, 169.30,
168.82, 156.14 (C-F, 2C, d, J = 235 Hz), 146.77, 143.64 (C-F, 2C, d, J = 2.0 Hz), 119.94,
115.67 (C-F, 2C, d, J = 22.0 Hz), 114.12 (C-F, 2C, d, J = 7.0 Hz), 85.65, 75.06, 72.54, 70.15,
67.64, 61.45, 40.36, 20.59, 20.46, 20.42, 20.01; HRMS (ESI) m/z calcd for C23H27FN4O9Na
(M+Na)+ 545.1660, found 545.1667.
1-(2,3,4,6-Tetra-O-acetyl-β-D-glucopyranosyl)-4-(4-bromophenylamino)-1,2,3-triazole
(4f): General procedure A was followed, starting with 4-bromoaniline (55.1 mg, 0.32 mmol).
The reaction mixture was stirred for 24 h and was purified by column chromatography (n-
hexane/EtOAc 3:2) provided the product as a yellow solid in 73% yield (114.0 mg); Rf =
26
0.097 (n-hexane/EtOAc 3:2); [α] ꢀꢁ-24.7 (c 0.5, CHCl3 ); mp = 181-183 °C; IR (film) 3399,
ꢂ
1
27
28
29
30
31
32
33
2924, 1755, 1595, 1500, 1369, 1228, 1040, 818, 598 cm-1; H NMR (400 MHz, CDCl3) δ
7.70 (s, 1H, H-triazole), 7.27 (d, J = 8.4 Hz, 2H, H-Ar), 6.55 (d, J = 8.4 Hz, 2H, H-Ar), 5.85
(d, J = 8.8 Hz, 1H, H-1), 5.45-5.37 (m, 2H, H-2, H-4), 5.27-5.18 (m, 1H, H-3), 4.44 (s, 2H,
H-3′), 4.29 (dd, J = 12.4, 4.8 Hz, 1H, H-6a), 4.14 (dd, J = 12.4, 1.6 Hz, 1H, H-6b), 3.99 (ddd,
J = 10.0, 4.8, 2.0 Hz, 1H, H-5), 2.08 (s, 3H, OAc), 2.07 (s, 3H, OAc), 2.03 (s, 3H, OAc), 1.83
(s, 3H, OAc); 13C NMR (100 MHz, CDCl3) δ 170.33, 169.74, 169.24, 168.74, 146.36,
146.28, 131.83 (2C), 120.01, 114.65 (2C), 109.52, 85.51, 74.92, 72.45, 70.09, 67.57, 61.39,
12

1
2
3
4
5
6
39.55, 20.52, 20.39, 20.35, 19.91; HRMS (ESI) m/z calcd for C23H27BrN4O9Na (M+Na)+
605.0859, found 605.0861.
1-(2,3,4,6-Tetra-O-acetyl-β-D-glucopyranosyl)-((benzylamino)methyl)-1,2,3-triazole
(4g): General procedure A was followed, starting with benzylamine (0.04mL, 0.32 mmol).
The reaction mixture was stirred for 24 h and was purified by column chromatography (n-
hexane/EtOAc 1:4) provided the product as a yellow solid in 58% yield (90.5 mg); Rf = 0.50
7
(n-hexane/EtOAc 1:4); [α] ꢀꢁ-27.6 (c 0.8, CHCl3 ); mp = 150-151 °C; IR (film) 2925, 2852,
ꢂ
8
9
1754, 1455, 1432, 1370, 1227, 1040, 738, 599 cm-1; 1H NMR (400 MHz, CDCl3) δ 7.85 (1H,
s, triazole-H), 7.42-7.21 (m, 5H, H-Ar), 5.88 (d, J = 9.2 Hz, 1H, H-1), 5.54 (t, J = 9.6 Hz, 1H,
H-2), 5.43 (t, J = 9.2 Hz, 1H, H-4), 5.25 (t, J = 9.6 Hz, 1H, H-3), 4.29 (dd, J = 12.8, 5.2 Hz,
1H, H-6a), 4.15 (dd, J = 12.0, 1.6 Hz, 1H, H-6b), 4.00 (ddd, J = 12.6, 4.8, 1.6 Hz, 1H, H-5),
3.79-3.60 (m, 4H, d, H-3′, H-5′), 2.07 (s, 3H, OAc), 2.06 (s, 3H, OAc), 2.04 (s, 3H, OAc),
10
11
12
13
14
15
16
17
18
19
20
13
1.84 (s, 3H, OAc); C NMR (100 MHz, CDCl3) δ 170.47, 169.93, 169.34, 169.00, 145.71,
138.55, 128.94 (2C), 128.34 (2C), 127.14, 121.43, 85.73, 75.10, 72.64, 70.32, 67.77, 61.64,
57.56, 47.30, 20.65, 20.50, 20.47, 20.11; HRMS (ESI) m/z calcd for C24H30N4O9Na (M+Na)+
541.1910, found 541.2856.
1-(2,3,4,6-Tetra-O-acetyl-β-D-glucopyranosyl)-4-(diallylamino)methyl-1,2,3-triazole
(4h): General procedure A was followed, starting with diallylamine (0.04 mL, 0.32 mmol).
The reaction mixture was stirred for 4 h and was purified by column chromatography (n-
hexane/EtOAc 7:3) provided the product as a white solide in 58% yield (81.0 mg); Rf = 0.12
21
(n-hexane/EtOAc 7:3); [α] ꢀꢁ -22.1 (c 0.5, CHCl3 ); mp = 135-137 °C; IR (film) 2925, 1755,
ꢂ
1
22
23
24
25
26
27
28
29
30
31
32
33
1642, 1369, 1223, 1039, 924 cm-1; H NMR (400 MHz, CDCl3) δ 7.69 (s, 1H, H-triazole),
5.93-5.80 (m, 3H, H-1, H-5′), 5.45-5.37 (m, 2H, H-3, H-4), 5.27-5.15 (m, 5H, H-2, H-6′),
4.30 ( dd, J = 12.4, 4.8 Hz, 1H, H-6a), 4.15 (dd, J = 12.4, 2.0 Hz, 1H, H-6b), 3.99 (ddd, J =
10.0, 4.8, 2.0 Hz, 1H, H-5), 3.77 (s, 2H, H-3′), 3.08 (d, J = 6.4 Hz, 4H, H-4′), 2.08 (s, 3H,
OAc), 2.06 (s, 3H, OAc), 2.02 (s, 3H, OAc), 1.85 (s, 3H, OAc); 13C NMR (100 MHz, CDCl3)
δ 170.37, 169.76, 169.27, 168.72, 145.98, 135.31 (2C), 120.73, 117.80 (2C), 85.59, 74.97,
72.51, 70.24, 67.68, 61.46, 56.22 (2C), 47.66, 20.56, 20.42, 20.38, 19.98; HRMS (ESI) m/z
calcd for C23H33N4O9 (M+H)+ 509.2248, found 509.2250.
1-(2,3,4,6-Tetra-O-acetyl-β-D-glucopyranosyl)-4-(dibutylamino)methyl-1,2,3-triazole
(4i): General procedure A was followed, starting with di-n-butylamine (0.05 mL, 0.32
mmol). The reaction mixture was stirred for 5 h and was purified by column chromatography
(n-hexane/EtOAc 7:3) provided the product as a white solid in 48% yield (72.9 mg); Rf =
13

1
0.15 (n-hexane/EtOAc 7:3); [α] ꢀꢁ -18.4 (c 0.5, CHCl3 ); mp = 118-120 °C; IR (film) 2957,
ꢂ
1
2
3
4
5
6
7
1756, 1369, 1226, 1039, cm-1; H NMR (400 MHz, CDCl3) δ 7.69 (s, 1H, H-triazole), 5.85
(d, J = 9.2 Hz, 1H, H-1), 5.46-5.37 (m, 2H, H-2, H-4), 5.24 (t, J = 9.6 Hz, 1H, H-2) 4.30 (dd,
J = 12.4, 4.8 Hz, 1H, H-6a), 4.14 (dd, J = 12.4, 1.6 Hz, 1H, H-6b), 3.99 (ddd, J = 10.0, 4.8,
1.6 Hz, 1H, H-5), 3.81 (d, J = 14.5 Hz, 1H, H-3′a), 3.76 (d, J = 15.0 Hz, 1H, H-3′b), 2.41 (t, J
= 7.5 Hz, 4H, H-4′), 2.08 (s, 3H, OAc), 2.06 (s, 3H, OAc), 2.02 (s, 3H, OAc), 1.85 (s, 3H,
OAc), 1.47 (quint, J = 7.6 Hz, 4H, H-5′), 1.29 (sext, J = 7.6 Hz, 4H, H-6′), 0.89 (t, J = 7.2
Hz, 6H, H-7′); 13C NMR (100 MHz, CDCl3) δ 170.46, 169.88, 169.34, 168.74, 146.43,
120.60, 85.70, 75.07, 72.67, 70.25, 67.76, 61.56, 53.44 (2C), 48.61, 29.23 (2C), 20.64, 20.56
(2C), 20.51, 20.48, 20.07, 14.01 (2C); HRMS (ESI) m/z calcd for C25H41N4O9 (M+H)+
541.2874, found 541.2864.
8
9
10
11
12
13
14
15
1-(2,3,4,6-Tetra-O-acetyl-β-D-glucopyranosyl)-4-((isopentylamino)methyl)-1,2,3-triazole
(4j): General procedure A was followed, starting with 1-amino-3-methylbutane (27.9 mg,
0.32 mmol). The reaction mixture was stirred for 3 h and was purified by column
chromatography (n-hexane/EtOAc 7:3) provided the product as a yellow solid in 51% yield
16
(67.1 mg); Rf = 0.42 (n-hexane/EtOAc 3:7); [α] ꢀꢁ-33.9 (c 0.5, CHCl3 ); mp = 192-194 °C; IR
ꢂ
1
17
18
19
20
21
22
23
24
25
26
27
28
29
(film) 2956, 2862, 1754, 1369, 1226, 1039 cm-1; H NMR (400 MHz, CDCl3) δ 7.84 (s,1H,
H-triazole), 5.87 (d, J = 9.2 Hz, 1H, H-1), 5.52 (t, J = 9.2 Hz, 1H, H-2), 5.43 (t, J = 9.6 Hz,
1H, H-4), 5.24 (t, J = 9.6 Hz, 1H, H-3), 4.29 (dd, J = 12.8, 5.2 Hz, 1H, H-6a), 4.15 (d, J =
12.0, Hz, 1H, H-6b), 4.00 (ddd, J = 10.0, 4.8, 1.6 Hz, 1H, H-5), 3.72 (dd, J = 30.8, 14.8 Hz,
2H, H-3′), 2.49 (s, 1H, H-N), 2.08 (s, 3H, OAc), 2.07 (s, 3H, OAc), 2.04 (s, 3H, 1.87), 1.87
13
(s, 3H, OAc), 1.60 (s, 11H, H-4′, H-5′, H-6′, H-7′); C NMR (100 MHz, CDCl3) δ 170.46,
169.91, 169.31, 168.94, 145.67, 121.34, 85.73, 75.08, 72.65, 70.33, 67.76, 61.63, 51.76,
47.56, 36.18, 26.23, 22.68, 22.63, 20.64, 20.50, 20.47, 20.13; HRMS (ESI) m/z calcd for
C22H34N4O9Na (M+Na)+ 521.2223, found 521.2233.
1-(2,3,4,6-Tetra-O-acetyl-β-D-galactopyranosyl)-4-(pyrrolidin-1-ylmethyl)-1,2,3-triazole
(6a): General procedure A was followed, starting with N-methylaniline (0.03 mL, 0.32
mmol). The reaction mixture was stirred for 6 h and was purified by column chromatography
n-hexane/EtOAc 3:2) provided the product as a brown solid in 95% yield (133.0 mg); Rf =
30
0.15 (n-hexane/EtOAc 3:2); [α] ꢀꢁ-12.2 (c 0.5, CHCl3 ); mp = 143-144 °C; IR (film) 2923,
ꢂ
1
31
32
1754, 1600, 1507, 1370, 1220, 1064, 752, 695 cm-1; H NMR (400 MHz, CDCl3) δ 761 (s,
1H, H-triazole), 7.30-7.22 (m, 2H, H-Ar), 6.81 (d, J = 8.0 Hz, 2H, H-Ar), 6.76 (t, J = 7.2 Hz,
14

1
2
1H, H-Ar), 5.78 (d, J = 9.2 Hz, 1H, H-1), 5.51 (d, J = 3.2 Hz, 1H, H-4), 5.48 (t, J = 10.0 Hz,
1H, H-2), 5.21 (dd, J = 10.0, 3.2 Hz, 1H, H-3), 4.63 (s, 2H, H-3′), 4.22-4.07 (m, 3H, H-6a, H-
6b, H-5), 3.01 (s, 3H, H- H-NCH3), 2.20 (s, 3H, OAc), 2.03 (s, 3H, OAc), 1.98 (s, 3H, OAc),
3
13
4
1.82 (s, 3H, OAc); C NMR (100 MHz, CDCl3) δ 170.29, 169.99, 169.75, 168.89, 149.10,
5
146.35, 129.22 (2C), 120.03, 117.26, 113.02 (2C), 86.21, 74.03, 70.73, 67.72, 66.79, 61.12,
48.69, 38.41, 20.65, 20.59, 20.42, 20.10; HRMS (ESI) m/z calcd for C24H30N4O9Na (M+Na)+
541.1910, found 541.1906.
6
7
8
1-(2,3,4,6-Tetra-O-acetyl-β-D-galactopyranosyl)-4-(naphthalen-2-ylamino)-1,2,3-triazole
(6b): General procedure A was followed, starting with 1-naphthylamine (45.8 mg, 0.32
mmol). The reaction mixture was stirred for 3 h and was purified by column chromatography
(n-hexane/EtOAc 1:3) provided the product as a brown solid in 48% yield (71.6 mg); Rf =
9
10
11
12
0.09 (n-hexane/EtOAc 1:3); [α] ꢀꢁ-13.6 (c 0.5, CHCl3 ); mp = 112-113 °C; IR (film) 3428,
ꢂ
1
13
14
15
16
17
18
19
20
21
22
23
24
25
2922, 1752, 1583, 1410, 1370, 1219, 1063, 923, 772 cm-1; H NMR (400 MHz, CDCl3) δ
7.83-7.77 (m, 1H, H-Ar), 7.75 (s, 1H, H-triazole), 7.74-7.70 (m, 1H, H-Ar), 7.43-7.34 (m,
2H, H-Ar), 7.23-7.17 (m, 2H, H-Ar), 6.57 (d, J = 7.2 Hz, 1H, H-Ar), 5.75 (d, J = 9.2 Hz, 1H,
H-1), 5.50-5.41 (m, 2H, H-4, H-2), 5.16 (dd, J = 10.4, 3.6 Hz, 1H, H-3), 4.57 (s, 2H, H-3′),
4.16-4.00 (m, 3H, H-6a, H-6b, H-5), 2.12 (s, 3H, OAc), 1.96 (s, 3H, OAc), 1.92 (s, 3H, OAc),
13
1.78 (s, 3H, OAc); C NMR (100 MHz, CDCl3) δ 170.32, 169.99, 169.79, 169.08, 146.73,
142.66, 134.29, 128.66, 126.53, 125.85, 124.92, 123.62, 120.36, 120.02, 118.18, 105.02,
86.30, 74.08, 70.78, 67.90, 66.89, 61.18, 40.15, 20.63 (2C), 20.46, 20.20; HRMS (ESI) m/z
calc. for C27H30N4O9Na (M+Na)+ 577.1910, found 577.1948.
1-(2,3,4,6-Tetra-O-acetyl-β-D-galactopyranosyl)-4-(3-fluorophenylamino)-1,2,3-triazole
(6c): General procedure A was followed, starting with 3-fluoroaniline (0.03 mL, 0.32 mmol).
The reaction mixture was stirred for 3 h and was purified by column chromatography (n-
hexane/EtOAc 3:2) provided the product as a brown solid in 75% yield (105.6 mg); Rf = 0.15
26
(n-hexane/EtOAc 3:2); [α] ꢀꢁ-12.9 (c 0.5, CHCl3 ); mp = 96-97 °C; IR (film) 3399, 2922,
ꢂ
1
27
28
29
30
31
32
33
1754, 1619, 1591, 1497, 1371, 1224, 1064, 764, 684 cm-1; H NMR (400 MHz, CDCl3) δ
7.76 (s, 1H, H-triazole), 7.11 (td, J = 6.8, 6.8 Hz, 1H, H-Ar), 6.46-6.39 (m, 2H, H-Ar), 6.33
(d, J = 11.6 Hz, 1H, H-Ar), 5.82 (d, J = 9.6 Hz, 1H, H-1), 5.56-5.49 (m, 2H, H-4, H-2), 5.23
(dd, J = 10.4, 3.2 Hz, 1H, H-3), 4.44 (s, 2H, H-3′), 4.25-4.10 (m, 3H, H-6a, H-6b, H-5), 2.04
(s, 3H, OAc), 2.00 (s, 3H, OAc), 1.85 (s, 3H, OAc), 1.25 (s, 3H, OAc); 13C NMR (100 MHz,
CDCl3) δ 170.25, 169.89, 169.71, 168.98, 163.92 (d, J = 242.0 Hz, C-F), 149.20 (d, J = 11.0
Hz, Cm-F), 146.29, 130.24 (d, J = 10.0 Hz, Cm-F), 120.08, 108.94 (d, J = 2.0 Hz, Cp-F),
15

1
2
3
4
5
6
7
104.31 (d, J = 22.0 Hz, Co-F), 99.75 (d, J = 26.0 Hz, Co-F), 86.09, 73.93, 70.64, 67.71, 66.82,
61.10, 39.60, 20.51, 20.50, 20.35, 20.01; HRMS (ESI) m/z calcd for C23H27FN4O9Na
(M+Na)+ 545.1660, found 545.1657
1-(2,3,4,6-Tetra-O-acetyl-β-D-galactopyranosyl)- 4-(4-fluorophenylamino)-1,2,3-triazole
(6d): General procedure A was followed, starting with 4-fluoroaniline (0.03 mL, 0.32 mmol).
The reaction mixture was stirred for 3 h and was purified by column chromatography (n-
hexane/EtOAc 3:2) provided the product as a yellow solid in 48% yield (68.0 mg); Rf = 0.04
8
(n-hexane/EtOAc 3:2); [α] ꢀꢁ-6.7 (c 0.6, CHCl3 ); mp = 166-167 °C; IR (film) 3396, 2923,
ꢂ
1
9
10
11
12
13
14
15
16
17
18
19
20
21
1755, 1514, 1371, 1219, 1064, 924 cm-1; H NMR (400 MHz, CDCl3) δ 7.75 (s, 1H, H-
triazole), 6.90 (t, J = 8.7 Hz, 2H, H-Ar), 6.63-6.56 (m, 2H, H-Ar), 5.81 (d, J = 9.3 Hz, 1H, H-
1), 5.53 (d, J = 3.6 Hz, 1H, H-4), 5.50 (t, J = 9.7 Hz, 1H, H-2), 5.23 (dd, J = 10.3, 3.3 Hz, 1H,
H-3), 4.42 (s, 2H, H-3′), 4.25-4.10 (m, 3H, H-6a, H-6b, H-5), 2.20 (s, 3H, OAc), 2.02 (s, 3H,
OAc), 2.00 (s, 3H, OAc), 1.84 (s, 3H, OAc); 13C NMR (100 MHz, CDCl3) δ 170.26, 169.88,
169.72, 168.98, 156.12 (d, J = 234.0 Hz, C-F), 146.69 (s, Cp-F), 143.74, 120.05, 115.63 (d, J
= 22.0 Hz, Co-F), 114.12 (d, J = 7.0 Hz, Cm-F), 86.14, 73.96, 70.68, 67.76, 66.82, 61.11,
40.43, 20.54 (2C), 20.39, 20.08; HRMS (ESI) m/z calcd for C23H27FN4O9Na (M+Na)+
545.1660, found 545.1663
1-(2,3,4,6-Tetra-O-acetyl-β-D-galactopyranosyl)- 4-(4-bromophenylamino)-1,2,3-triazole
(6e): General procedure A was followed, starting with 4-bromoaniline (55.1 mg, 0.32 mmol).
The reaction mixture was stirred for 3 h and was purified by column chromatography (n-
hexane/EtOAc 3:2) provided the product as a yellow solid in 71% yield (110.0 mg); Rf = 0.25
22
(n-hexane/EtOAc 1:1); [α] ꢀꢁ-14.4 (c 0.5, CHCl3 ); mp = 150-151 °C; IR (film) 3398, 2923,
ꢂ
1
23
24
25
26
27
28
29
30
31
32
33
1752, 1595, 1501, 1270, 1219, 1066, 923, 599 cm-1; H NMR (400 MHz, CDCl3) δ 7.68 (s,
1H, H-triazole), 7.19 (d, J = 8.8 Hz, 2H, H-Ar), 6.47 (d, J = 8.0 Hz, 2H, H-Ar), 5.75 (d, J =
9.2 Hz, 1H, H-1), 5.47 (d, J = 1.6 Hz, 1H, H-4), 5.43 (t, J = 9.6 Hz, 1H, H-2), 5.16 (dd, J =
12.0, 4.0 Hz, 1H, H-3), 4.36 (s, 2H, H-3′), 4.18-4.01 (m, 3H, H-6a, H-6b, H-5), 2.14 (s, 3H,
OAc), 1.97 (s, 3H, OAc), 1.94 (s, 3H, OAc), 1.77 (s, 3H, OAc); 13C NMR (100 MHz, CDCl3)
δ 170.28, 169.90, 169.73, 169.03, 146.38, 131.94 (2C), 120.07, 114.77 (2C), 109.74, 86.21,
74.03, 70.69, 67.75, 66.81, 61.11, 39.80, 20.59, 20.58, 20.42, 20.12; HRMS (ESI) m/z calcd
for C23H27BrN4O9 (M+Na)+ 605.0859, found 605.0853.
1-(2,3,4,6-Tetra-O-acetyl-β-D-galactopyranosyl)-4-(diallylamino)-1,2,3-triazole (6f):
General procedure A was followed, starting with diallylamine (0.04 mL, 0.32 mmol). The
reaction mixture was stirred for 6 h and was purified by column chromatography (n-
16

1
2
hexane/EtOAc 3:2) provided the product as a brown solid in75% yield (109.2 mg); Rf = 0.17
(n-hexane/EtOAc 3:2); [α] ꢀꢁ-8.9 (c 0.5, CHCl3 ); mp = 112-113 °C; IR (film) 2923, 1754,
ꢂ
3
4
1642, 1371, 1219, 1064, 923 cm-1 ; 1H NMR (400 MHz, CDCl3) δ 7.75 (s, 1H, H-triazole),
5.87 (ddt, J = 17.6, 10.4, 6.4 Hz, 2H, H-5′), 5.82 (d, J = 9.6 Hz, 1H, H-1), 5.58-5.50 (m, 2H,
H-4, H-2), 5.27-5.15 (m, 5H, H-3, H-6′), 4.25-4.10 (m, 3H, H-6a, H-6b, H-5), 3.78 (s, 2H, H-
3′), 3.10 (d, J = 6.4 Hz, 4H, H-4′), 2.22 (s, 3H, OAc), 2.04 (s, 3H, OAc), 2.00 (s, 3H, OAc),
1.87 (s, 3H, OAc); 13C NMR (100 MHz, CDCl3) δ 170.25, 169.90, 169.71, 168.93, 146.04,
135.29 (2C), 120.85, 117.89 (2C), 86.16, 73.92, 70.68, 67.86, 66.84, 61.12, 56.28 (2C),
47.82, 20.58, 20.55, 20.40, 20.12; HRMS (ESI) m/z calcd for C23H33N4O9 (M+H)+ 509.2248,
found 509.2245.
5
6
7
8
9
10
11
12
13
14
1-(2,3,4,6-Tetra-O-acetyl-β-D-galactopyranosyl)-4-(dibutylamino)-1,2,3-triazole
(6g):
General procedure A was followed, starting with di-n-butylamine (0.05 mL, 0.32 mmol). The
reaction mixture was stirred for 6 h and was purified by column chromatography (n-
hexane/EtOAc 3:2) provided the product as a yellow solid in 68% yield (100.0 mg); Rf = 0.15
15
(n-hexane/EtOAc 3:2); [α] ꢀꢁ-4.2 (c 0.5, CHCl3 ); mp = 106-107 °C; IR (film) 2933, 1756,
ꢂ
16
17
18
19
20
1370, 1219, 1065, cm-1 ; 1H NMR (400 MHz, CDCl3) δ 7.75 (s, 1H, H-triazole), 5.82 (d, J =
9.6 Hz, 1H, H-1), 5.59-5.51 (m, 2H, H-4, H-2), 5.23 (dd, J = 10.4, 3.2 Hz, 1H, H-3), 4.25-
4.10 (m, 3H, H-6a, H-6b, H-5), 3.79 (s, 2H, H-3′), 2.43 (t, J = 7.2 Hz, 4H, H-4′), 2.22 (s, 3H,
OAc), 2.04 (s, 3H, OAc), 2.00 (s, 3H, OAc), 1.87 (s, 3H, OAc), 1.48 (quint, J = 7.6 Hz, 4H,
H-5′), 1.30 (sext, J = 7.6 Hz, 4H, H-6′), 0.90 (t, J = 7.6 Hz, 6H, H-7′); 13C NMR (100 MHz,
CDCl3) δ 170.24, 169.91, 169.73, 168.85, 145.96, 120.87, 86.17, 73.90, 70.75, 67.84, 66.85,
61.12, 53.27 (2C), 48.52, 28.94 (2C), 20.57, 20.54, 20.51 (2C), 20.40, 20.12, 13.94 (2C);
HRMS (ESI) m/z calcd for C25H41N4O9 (M+H)+ 541.2874, found 541.2879.
21
22
23
24
25
26
27
1-(2,3,4-Tri-O-acetyl-β-D-xylopyranosyl)-4-(butyl(phenyl)amino)-1,2,3-triazole
(10a):
General procedure A was followed, starting with N-n-butylaniline (0.06 mL, 0.40 mmol).
The reaction mixture was stirred for 15 h and was purified by column chromatography (n-
hexane/EtOAc 3:2) provided the product as a brown solid in 88% yield (143.1 mg); Rf = 0.24
28
(n-hexane/EtOAc 3:2); [α] ꢀꢁ-56.9 (c 0.5, CHCl3 ); mp = 130-131 °C; IR (film) 2957, 1759,
ꢂ
29
30
31
32
1599,1506, 1370, 1218, 1039, 749, 693 cm-1 ; 1H NMR (400 MHz, CDCl3) δ 7.47 (s, 1H, H-
triazole), 7.20 (t, J =7.6 Hz, 2H, H-Ar), 6.75-6.65 (m, 3H, H-Ar), 5.71 (d, J = 9.2 Hz, 1H, H-
1), 5.37 (t, J = 9.0 Hz, 1H, H-3), 5.30 (t, J = 9.0 Hz, 1H, H-2), 5.15-5.05 (m, 1H, H-4), 4.61
(s, 2H, H-3′), 4.24 (dd, J = 11.6, 5.6 Hz, 1H, H-5a), 3.54 (dd, J = 11.6, 10.8 Hz, 1H, H-5b),
17

1
2
3.34 (t, J = 8.4 Hz, 2H, H-4′), 2.05 (s, 3H, OAc), 2.02 (s, 3H, OAc), 1.81 (s, 3H, OAc), 1.60
(quint, J = 7.6 Hz, 2H, H-5′), 1.35 (sext, J = 7.6 Hz, 2H, H-6′), 0.94 (t, J = 7.0 Hz, 3H, H-7′);
13C NMR (100 MHz, CDCl3) δ 169.86, 169.68, 168.77, 147.95, 147.01, 129.29 (2C), 120.04,
116.63, 112.58 (2C), 86.27, 72.08, 70.37, 68.41, 65.49, 51.07, 46.70, 29.49, 20.59, 20.54,
20.26, 20.06, 13.94; HRMS (ESI) m/z calcd for C24H32N4O7Na (M+Na)+ 511.2169, found
511.2170.
3
4
5
6
7
1-(2,3,4-Tri-O-acetyl-β-D-xylopyranosyl)-4-(diallylamino)-1,2,3-triazole (10b): General
procedure A was followed, starting with diallylamine (0.05 mL, 0.40 mmol). The reaction
mixture was stirred for 6 h and was purified by column chromatography (n-hexane/EtOAc
3:2) provided the product as a white solid in 76% yield (110.0 mg); Rf = 0.14 (n-
8
9
10
11
hexane/EtOAc 3:2); [α] ꢀꢁ-60.0 (c 0.6, CHCl3 ); mp = 115-117°C; IR (film) 2924, 1759,
ꢂ
1
12
13
14
15
16
17
18
19
20
21
22
23
1643, 1371, 1218, 1041, 934 cm-1 ; H NMR (400 MHz, CDCl3) δ 7.68 (s,1H, H- triazole),
5.87 (ddt, J = 17.6, 10.4, 6.4 Hz, 2H, H-5′), 5.76 (d, J = 8.8 Hz, 1H, H-1), 5.41 (t, J = 9.2 Hz,
1H, H-3), 5.35 (t, J = 9.2 Hz, 1H, H-2), 5.26-5.10 (m, 5H, H-6′, H-4), 4.30 (dd, J = 11.6, 5.6
Hz, 1H, H-5a), 3.78 (s, 2H, H-3′), 3.59 (dd, 1H, J = 11.2, 10.8 Hz, 1H, H-5b), 3.08 (d, J = 6.0
Hz, 4H, H-4′), 2.07 (s, 3H, OAc), 2.04 (s, 3H, OAc), 1.86 (s, 3H, OAc); 13C NMR (100 MHz,
CDCl3) δ 169.79, 169.71, 168.87, 145.92, 135.46 (2C), 120.72, 117.77 (2C), 86.29, 72.06,
70.50, 68.46, 65.53, 56.25 (2C), 47.70, 20.58, 20.53, 20.08; HRMS (ESI) m/z calc. for
C20H29N4O7 (M+H)+ 437.2036, found 437.2046.
1-(2,3,4-Tri-O-acetyl-β-D-xylopyranosyl)-4-(dibutylamino)-1,2,3-triazole (10c): General
procedure A was followed, starting with di-n-butylamine (0.07 mL, 0.40 mmol). The reaction
mixture was stirred for 6 h and was purified by column chromatography (n-hexane/EtOAc
3:2) provided the product as a white solid in 76% yield (119.7 mg); Rf = 0.14 (n-
24
hexane/EtOAc 3:2); [α] ꢀꢁ-51.8 (c 0.8, CHCl3 ); mp = 121-122°C; IR (film) 2957, 1760,
ꢂ
1
25
26
27
28
29
30
31
32
1372, 1245, 1040 cm-1; H NMR (400 MHz, CDCl3) δ 7.67 (s, 1H, H-triazole), 5.76 (d, J =
8.4 Hz, 1H, H-1), 5.41 (t, J = 9.0 Hz, 1H, H-3), 5.36 (t, J = 9.0 Hz, 1H, H-2), 5.20-5.10 (m,
1H, H-4), 4.29 (dd, J = 11.6, 5.6 Hz, 1H, H-5a), 3.80 (brs, 2H, H-3′), 3.58 (dd, J = 11.2, 10.8
Hz, 1H, H-5b), 2.41 (brt, J = 7.2 Hz, 4H, H-4′), 2.07 (s, 3H, OAc), 2.04 (s, 3H, OAc), 1.86 (s,
3H, OAc), 1.47 (quint, J = 7.2 Hz, 4H, H-5′), 1.28 (sext, J = 7.5 Hz, 4H, H-6′), 0.89 (t, J =
13
7.2 Hz, 6H, H-7′); C NMR (100 MHz, CDCl3) δ 169.82, 169.72, 168.82, 146.32, 120.47,
86.30, 72.13, 70.45, 68.47, 65.54, 53.43 (2C), 48.55, 29.34 (2C), 20.55 (4C), 20.08, 14.01
(2C); HRMS (ESI) m/z calcd for C22H37N4O9 (M+H)+ 469.2662, found 469.2673.
18

1
2
3
4
1-(2,3,4-Tri-O-acetyl-β-L-arabinopyranosyl)-4-(butyl(phenyl)amino)-1,2,3-triazole
(11a): General procedure A was followed, starting with N-n-butylaniline (0.06 mL, 0.40
mmol). The reaction mixture was stirred for 2 h and was purified by column chromatography
(n-hexane/EtOAc 3:2) provided the product as a brown solid in 55% yield (91.0 mg); Rf =
5
0.24 (n-hexane/EtOAc 3:2); [α] ꢀꢁ-22.4 (c 0.5, CHCl3 ); mp = 179-180°C; IR (film) 2921,
ꢂ
1
6
7
1749, 1597, 1508, 1371, 1219, 1058, 746, 693 cm-1; H NMR (400 MHz, CDCl3) δ 7.56 (s,
1H, H-triazole), 7.21 (t, J =7.6 Hz, 2H, H-Ar), 6.75-6.66 (m, 3H, H-Ar), 5.68 (d, J = 9.2 Hz,
1H, H-1), 5.52 (t, J = 10.0 Hz, 1H, H-2), 5.40 (brs, 1H, H-4), 5.22 (dd, J = 10.0, 3.2 Hz, 1H,
H-3), 4.62 (s, 2H, H-3′), 4.14 (d, J = 13.2 Hz, 1H, H-5a), 3.90 (d, J = 13.6 Hz, 1H, H-5b),
3.35 (t, J = 7.6 Hz, 2H, H-4′), 2.19 (s, 3H, OAc), 2.00 (s, 3H, OAc), 1.84 (s, 3H, OAc), 1.62
(m, 2H, H-5′), 1.35 (sext, J = 7.6 Hz, 2H, H-6′), 0.95 (t, J = 7.2 Hz, 3H, H-7′); 13C NMR (100
MHz, CDCl3) δ 170.20, 169.85, 168.90, 148.08, 147.02, 129.30 (2C), 120.05, 116.53, 112.53
(2C), 86.73, 70.55, 68.03, 67.65, 67.32, 50.92, 46.75, 29.33, 20.98, 20.54, 20.29, 20.20,
13.97; HRMS (ESI) m/z calcd for C24H32N4O9Na (M+Na)+ 511.2169, found 511.2172.
8
9
10
11
12
13
14
15
16
17
18
1-(2,3,4-Tri-O-acetyl-β-L-arabinopyranosyl)-4-(diallylamino)-1,2,3-triazole
(11b):
General procedure A was followed, starting with diallylamine (0.05 mL, 0.40 mmol). The
reaction mixture was stirred for 6 h and was purified by column chromatography (n-
hexane/EtOAc 1:1) provided the product as a brown solid in 51% yield (74.3 mg); Rf = 0.07
19
(n-hexane/EtOAc 1:1); [α] ꢀꢁ-7.0 (c 0.9, CHCl3 ); mp = 126-128°C; IR (film) 2924, 1747,
ꢂ
1
20
21
22
23
24
25
26
27
28
29
30
31
1643, 1373, 1223, 1062, 917 cm-1; H NMR (400 MHz, CDCl3) δ 7.75 (s, 1H, H-triazole),
5.95-5.80 (m, 2H, H-5′), 5.73 (d, J = 9.2 Hz, 1H, H-1), 5.57 (t, J = 9.6 Hz, 1H, H-2), 5.43
(brs, 1H, H-4), 5.28-5.13 (m, 5H, H-3, H-6′), 4.18 (d, J = 13.2 Hz, 1H, H-5a), 3.94 (d, J =
13.6 Hz, 1H, H-5b), 3.78 (s, 2H, H-3′), 3.09 (d, J = 6.0 Hz, 4H, H-4′), 2.22 (s, 3H, OAc),
2.02 (s, 3H, OAc), 1.87 (s, 3H, OAc); 13C NMR (100 MHz, CDCl3) δ 170.06, 169.78, 168.98,
145.83, 135.31 (2C), 120.81, 117.88 (2C), 86.63, 70.46, 68.15, 67.70, 67.23, 56.23 (2C),
47.79, 20.87, 20.48, 20.15; HRMS (ESI) m/z calcd for C20H28N4O8 (M+H)+ 437.2036, found
437.2034
1-(2,3,4-Tri-O-acetyl-α-D-arabinopyranosyl)-4-((butyl(phenyl)amino))-1,2,3-triazole
(12a): General procedure A was followed, starting with N-n-butylaniline (0.06 mL, 0.40
mmol). The reaction mixture was stirred for 2 h and was purified by column chromatography
(n-hexane/EtOAc 3:2) provided the product as a brown solid in 51% yield (83.0 mg); Rf =
32
0.17 (n-hexane/EtOAc 3:2); [α] ꢀꢁ+8.8 (c 0.5, CHCl3 ); mp = 167-168°C; IR (film) 2958,
ꢂ
19

1
1
2
3
4
5
6
1750, 1599, 1506, 1371, 1220, 1062, 749, 693 cm-1; H NMR (400 MHz, CDCl3) δ 7.56 (s,
1H, H- triazole), 7.21 (t, J =8.0 Hz, 2H, H-Hb), 6.75-6.65 (m, 3H, H-Ha,H-Hc), 5.68 (d, J =
9.2 Hz, 1H, H-1), 5.52 (t, J = 10.0 Hz, 1H, H-2), 5.40 (brs, 1H, H-4), 5.20 (dd, J = 10.0, 2.8
Hz, 1H, H-3), 4.62 (s, 2H, H-3′), 4.14 (d, J = 12.8 Hz, 1H, H-5a), 3.90 (d, J = 13.2 Hz, 1H,
H-5b), 3.35 (t, J = 7.6 Hz, 2H, H-4′), 2.19 (s, 3H, OAc), 2.00 (s, 3H, OAc), 1.83 (s, 3H,
OAc), 1.61 (quint, J = 7.20 Hz, 2H, H-5′), 1.36 (sext, J = 7.60 Hz, 2H, H-6′), 0.95 (t, J = 7.20
Hz, 3H, H-7′); 13C NMR (100 MHz, CDCl3) δ 170.11, 169.75, 168.81, 148.00, 146.89,
129.21 (2C), 119.97, 116.44, 112.46 (2C), 86.59, 70.47, 67.97, 67.60, 67.21, 50.83, 46.65,
29.25, 20.88, 20.44, 20.19, 20.09, 13.88; HRMS (ESI) m/z calcd for C24H32N4O7Na (M+Na)+
511.2169, found 511.2175.
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
General Procedure (B): The solution of amine (0.32 mmol) in CH2Cl2 1 mL was added
DIPEA (0.05 mL, 0.27 mmol), propargyl bromide (0.04 mL, 0.54 mmol) and TBAI (18.5
mg, 0.05 mmol). The reaction mixture was stirred at room temperature until TLC showed the
complete conversion (1 h-8 h). Then the reaction mixture was added H2O 2 mL, glycosyl
azide (100 mg, 0.27 mmol) and CuI (5.7 mg, 0.03 mmol). The reaction mixture was
continuously stirred at room temperature until completion of reaction as indicated by
appearance of a new spot on the TLC plates. The reaction mixture was diluted with CH2Cl2
and poured into EDTA solution. The mixture was stirred for 5 min. then the reaction mixture
was extracted with CH2Cl2. The organic layers were dried over anhydrous Na2SO4 and
concentrated under reduced pressure to afford the crude compound which was further
purified by siliga gel column chromatography.
1-(2,3,4,6-Tetra-O-acetyl-β-D-glucopyranosyl)-4-(pyrrolidin-1-ylmethyl)-1,2,3-triazole
(4k): General procedure B was followed, starting with pyrolidine (0.026 mL, 0.32 mmol) The
reaction mixture was stirred for 4 h and was purified by siliga gel column chromatography
(CH2Cl2/MeOH 19:1) provided the product as a brown solid in 54% yield (72.0 mg); Rf =
26
0.27 (CH2Cl2/MeOH 19:1); [α] ꢀꢁ-17.6 (c 0.5, CHCl3 ); mp = 143-145 °C; IR (film) 2965,
ꢂ
1
27
28
29
30
31
32
1754, 1369, 1224, 1039 cm-1 ; H NMR (400 MHz, CDCl3) δ 7.74(d, J = 2.0 Hz, 1H, H-
triazole), 5.84 (dd, J = 7.0, 2.0 Hz, 1H, H-1), 5.40 (dd, J = 6.8, 2.4 Hz, 2H, H-4, H-2), 5.22 (t
J = 9.6 Hz, 1H, H-3), 4.28 (dd, J = 12.4, 4.8 Hz, 1H, H-6a), 4.12 (dd, J = 12.4, 2.0 Hz, 1H,
H-6b), 3.98 (ddd, J = 10.0, 4.8, 2.0 Hz, 1H, H-5), 3.58 (dd, J = 8.0, 2.0 Hz, 2H, H-3′), 2.56
(d, J = 2.0 Hz, 4H, H-4′), 2.07 (s, 3H, OAc), 2.05 (s, 3H, OAc), 2.00 (s, 3H, OAc), 1.85 (s,
3H, OAc), 1.78 (t, J = 2.0 Hz, 4H, H-5′); 13C NMR (100 MHz, CDCl3) δ 170.4, 169.8, 169.2,
20

1
2
3
4
5
6
169.0, 146.4, 120.5, 85.7, 75.0, 72.6, 70.3, 67.7, 61.5, 53.8 (2C), 50.4, 23.4 (2C), 20.6, 20.5,
20.4, 20.1; HRMS (ESI) m/z calc for C21H31N4O9 (M+H)+ 483.2091, found 483.2088.
1-(2,3,4,6-Tetra-O-acetyl-β-D-glucopyranosyl)-4-(morpholinomethyl)-1,2,3-triazole (4l):
General procedure B was followed, starting with morpholine (0.03 mL, 0.32 mmol). The
reaction mixture was stirred for 3 h and was purified by siliga gel column chromatography
(n-hexane/EtOAc 0:1) provided the product as a white solid in 96% yield (133.0 mg); Rf =
7
0.15 (n-hexane/EtOAc 0:1); [α] ꢀꢁ-18.6 (c 0.5, CHCl3 ); mp = 151-154 °C; IR (film) 2924,
ꢂ
8
9
1755, 1370, 1226, 1040 cm-1; 1H NMR (400 MHz, CDCl3) δ 7.76 (brs, 1H, H-triazole), 5.85
(d, J = 8.4 Hz, 1H, H-1), 5.44-5.35 (m, 2H, H-2, H-4), 5.22 (t, J = 9.2 Hz, 1H, H-3), 4.30 (dd,
J = 12.8, 4.8 Hz, 1H, H-6a), 4.14 (dd, J = 12.4, 2.0 Hz, 1H, H-6b), 3.99 (ddd, J = 10.4, 4.8,
2.0 Hz, 1H, H-5), 3.72 (brs, 6H, H-3′, H-5′), 2.52 (brs, 4H, H-4′), 2.08 (s, 3H, OAc), 2.06 (s,
10
11
12
13
14
15
16
17
18
19
13
3H, OAc), 2.01 (s, 3H, OAc), 1.85 (s, 3H, OAc); C NMR (100 MHz, CDCl3) δ 170.28,
169.66, 169.20, 168.71, 144.65, 120.96, 85.53, 74.88, 72.32, 70.27, 67.56, 66.56 (2C), 61.38,
53.28, 53.03 (2C), 20.49, 20.35, 20.30, 19.93; HRMS (ESI) m/z calcd for C21H31N4O10
(M+H)+ 499.2035, found 499.2038.
1-(2,3,4,6-Tetra-O-acetyl-β-D-galactopyranosyl)-4-(pyrrolidin-1-ylmethyl)-1,2,3-triazole
(6h): General procedure B was followed, starting with pyrolidine (0.026 mL, 0.32 mmol).
The reaction mixture was stirred for 24 h and was purified by siliga gel column
chromatography (CH2Cl2/MeOH 19:1) provided the product as a brown solid in 51% yield
20
(66.7 mg); Rf = 0.27 (CH2Cl2/MeOH 19:1); [α] ꢀꢁ-5.6 (c 0.5, CHCl3 ); mp = 150-152 °C; IR
ꢂ
1
21
22
23
24
25
26
27
28
29
30
31
32
(film) 2925, 1752, 1371, 1221, 1063 cm-1 ; H NMR (400 MHz, CDCl3) δ 7.96 (s, 1H, H-
triazole), 5.80 (d, J = 9.2 Hz, 1H, H-1), 5.53 (d, J = 2.8 Hz, 1H, H-4), 5.51 (t, J = 9.6 Hz, 1H,
H-2), 5.23 (dd, J = 10.0, 3.6 Hz, 1H, H-3), 4.24-4.10 (m, 3H, H-6a, H-6b, H-5), 3.99 (brs,
4H, H-4′), 3.96 (s, 2H, H-3′), 2.82-2.72 (m, 4H, H-5′), 2.21 (s, 3H, OAc), 2.03 (s, 3H, OAc),
2.00 (s, 3H, OAc), 1.87 (s, 3H, OAc); 13C NMR (100 MHz, CDCl3) δ 170.31, 169.95, 169.78,
169.01, 146.22, 120.76, 86.23, 73.93, 70.75, 67.96, 66.84, 61.18, 53.83 (2C), 50.53, 23.49
(2C), 20.61 (2C), 20.45, 20.20; HRMS (ESI) m/z calcd for C21H31N4O9 (M+H)+ 483.2091,
found 483.2088.
1-(2,3,4,6-Tetra-O-acetyl-β-D-galactopyranosyl)-(morpholinomethyl)-1,2,3-triazole (6i):
General procedure B was followed, starting with morpholine (0.03 mL, 0.32 mmol). The
reaction mixture was stirred for 2 h and was purified by siliga gel column chromatography
(n-hexane/EtOAc 0:1) provided the product as a yellow solid in 90% yield (120.4 mg); Rf =
33
0.12 (n-hexane/EtOAc 0:1); [α] ꢀꢁ-2.4 (c 0.5, CHCl3 ); mp = 140-142 °C; IR (film) 2926,
ꢂ
21

1
1
2
3
4
1752, 1371, 1221, 1065, cm-1 ; H NMR (400 MHz, CDCl3) δ 7.79 (s, 1H, H-triazole), 5.82
(d, J = 9.2 Hz, 1H, H-1), 5.54 (d, J = 2.8 Hz, 1H, H-4), 5.49 (t, J = 9.6 Hz, 1H, H-2), 5.24
(dd, J = 10.0, 3.2 Hz, 1H, H-3), 4.25-4.09 (m, 3H, H-6a, H-6b, H-5), 3.73 (brs, 4H, H-5′),
3.69 (s, 2H, H-3′), 2.51 (brs, 4H, H-4′), 2.21 (s, 3H, OAc), 2.04 (s, 3H, OAc), 2.00 (s, 3H,
13
5
6
OAc), 1.87 (s, 3H, OAc); C NMR (100 MHz, CDCl3) δ 170.20, 169.82, 169.64, 168.97,
144.57, 121.11, 86.13, 73.90, 70.53, 67.92, 66.76, 66.64 (2C), 61.08, 53.42, 53.12 (2C),
20.53, 20.52, 20.35, 20.12; HRMS (ESI) m/z calcd for C21H32N4O10 (M+H)+ 499.2040, found
499.2038.
7
8
9
1-(2,3,4-Tri-O-acetyl-β-D-xylopyranosyl)-4-(morpholinomethyl)-1,2,3-triazole
(10d):
10
11
12
General procedure B was followed, starting with morpholine (0.04 mL, 0.40 mmol). The
reaction mixture was stirred for 2 h and was purified by siliga gel column chromatography
(n-hexane/EtOAc 0:1) provided the product as a white solid in 48% yield (68.0 mg); Rf =
13
0.14 (n-hexane/EtOAc 0:1); [α] ꢀꢁ -56.6 (c 0.6, CHCl3 ); mp = 189-190°C; IR (film) 2957,
ꢂ
1
14
15
16
17
18
19
20
21
22
23
24
1759, 1372, 1218, 1042 cm-1; H NMR (400 MHz, CDCl3) δ 7.71 (s, 1H, H- triazole), 5.76
(d, J = 9.0 Hz, 1H, H-1), 5.42 (t, J = 9.0 Hz, 1H, H-3), 5.33 (t, J = 9.0 Hz, 1H, H-2), 5.10-
5.10 (m, 1H, H-4), 4.29 (dd, J = 11.6, 5.6 Hz, 1H, H-5a), 3.71 (t, J = 4.4 Hz, 4H, H-5′), 3.69
(s, 2H, H-3′), 3.59 (dd, J = 11.2, 10.8 Hz, 1H, H-5b), 2.49 (brt, J = 4.0 Hz, 4H, H-4′), 2.07 (s,
13
3H, OAc), 2.05 (s, 3H, OAc), 1.87 (s, 3H, OAc); C NMR (100 MHz, CDCl3) δ 169.76,
169.70, 168.94, 144.96, 120.83, 86.34, 71.93, 70.52, 68.40, 66.81 (2C), 65.54, 53.48, 53.17
(2C), 20.57, 20.52, 20.10; HRMS (ESI) m/z calcd for C18H27N4O10 (M+H)+ 427.1829, found
427.1842.
1-(2,3,4-Tri-O-acetyl-α-D-arabinopyranosyl)-4-(morpholinomethyl)-1,2,3-triazole (12b):
General procedure B was followed, starting with morpholine (0.04 mL, 0.40 mmol). The
reaction mixture was stirred for 2 h and was purified by siliga gel column chromatography
25
(n-hexane/EtOAc 0:1) provided the product as a white solid in 72% yield (101.0 mg); [α] ꢀꢁ-
ꢂ
26
27
28
29
30
31
32
11.1 (c 0.5, CHCl3 ); Rf = 0.15 (MeOH/EtOAc 1:9); mp = 165-168°C; IR (film) 2922, 1749,
1
1372, 1220, 1063 cm-1; H NMR (400 MHz, CDCl3) δ 7.83 (s, 1H, H -triazole), 5.73 (d, J =
9.2 Hz, 1H, H-1), 5.54 (t, J = 10.0 Hz, 1H, H-2), 5.44 (br s, 1H, H-4), 5.24 (dd, J = 10.0, 3.2
Hz, 1H, H-3), 4.19 (dd, J = 13.2, 1.6 Hz, 1H, H-5a), 3.94 (dd, J = 13.6, 1.2 Hz, 1H, H-5b),
3.74 (t, J = 4.8 Hz, 4H, H-5′), 3.71 (s, 2H, H-3′), 2.53 (brt, J = 4.1 Hz, 4H, H-4′), 2.22 (s,
13
3H,OAc), 2.02 (s, 3H, OAc), 1.88 (s, 3H, OAc); C NMR (100 MHz, CDCl3) δ 169.87,
169.58, 168.90, 143.94, 121.19, 86.44, 70.17, 68.13, 67.54, 67.07, 66.40, 66.31, 52.80, 51.78,
22

1
2
47.38, 20.68, 20.31, 20.02; HRMS (ESI) m/z calcd for C18H26N4NaO8 (M+Na)+ 449.1648,
found 449.1648
3
General Procedure (C): The solution of amine (0.13 mmol) in CH2Cl2 1 mL was added
DIPEA (0.05 mL, 0.27 mmol), propargyl bromide (0.04 mL,0.59 mmol) and TBAI (18.4 mg,
0.05 mmol). The reaction mixture was stirred at room temperature until TLC showed the
complete conversion (3 h-4 h). Then the reaction mixture was added H2O 2 mL, glycosyl
azide (100 mg, 0.27 mmol) and CuI (5.7 mg, 0.03 mmol). The reaction mixture was
continuously stirred at room temperature until completion of reaction as indicated by
appearance of a new spot on the TLC plates. The reaction mixture was diluted with CH2Cl2
and poured into EDTA solution. The mixture was stirred for 5 min. then the reaction mixture
was extracted with CH2Cl2. The organic layers were dried over anhydrous Na2SO4 and
concentrated under reduced pressure to afford the crude compound which was further
purified by siliga gel column chromatography.
4
5
6
7
8
9
10
11
12
13
14
15
16
17
di-1-(2,3,4,6-Tetra-O-acetyl-β-D-glucopyranosyl)-4-(acetoxymethyl)-1,2,3-triazole (13a):
General procedure C was followed, starting with 3,4-dimethoxyaniline (19.9 mg, 0.13
mmol). The reaction mixture was stirred for 18 h and was purified by siliga gel column
chromatography (n-hexane/EtOAc 0:1) provided the product as a brown solid in 40% yield
18
(62.9 mg); Rf = 0.12 (n-hexane/EtOAc 2:3); [α] ꢀꢁ-26.4 (c 0.7, CHCl3 ); mp = 166-168 °C; IR
ꢂ
1
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
(film) 2925, 1739, 1520, 1449, 1367, 1213, 1034, 924, 599 cm-1; H NMR (400 MHz,
CDCl3) δ 7.68 (s, 2H, H-triazole), 6.75 (t, 1H, J =8.8 Hz, H-Ar), 6.52 (d, 1H, J = 2.4 Hz, H-
Ar), 6.36 (dd, 1H, J = 8.8, 2.4 Hz, H-Ar), 5.84 (d, 2H, J = 9.6 Hz, H-1), 5.49 (t, 2H, J = 9.6
Hz, H-3), 5.40 (t, 2H, J = 9.6 Hz, H-4), 5.19 (t, 2H, J = 9.6 Hz, H-2), 4.56 (d, 4H, J = 10.8
Hz, H-3′), 4.26 (dd, 2H, J = 12.8, 5.2 Hz, H-6a), 4.14 (dd, 2H, J = 12.8, 1.5 Hz, H-6b), 3.97
(ddd, 2H, J = 10.0, 4.8, 2.0 Hz, H-5), 3.80 (s, 6H, H-CH3), 2.06 (s, 6H, OAc), 2.05 (s, 6H,
13
OAc), 2.02(s, 6H, OAc), 1.80 (s, 6H, OAc); C NMR (100 MHz, CDCl3) δ 170.43 (2C),
169.90 (2C), 169.27 (2C), 168.96 (2C), 149.57, 146.28 (2C), 142.89, 142.38, 120.74 (2C),
112.53, 106.92, 101.22, 85.68 (2C), 75.09 (2C), 72.54 (2C), 70.08 (2C), 67.67 (2C), 61.57
(2C), 56.36, 55.76, 48.06, 29.63, 20.61 (2C), 20.47 (2C), 20.42 (2C), 19.98 (2C); HRMS
(ESI) m/z calcd for C42H53N7O20 (M+H)+ 976.3424, found 976.3486.
di-1-(2,3,4,6-Tetra-O-acetyl-β-D-glucopyranosyl)-4-(3-methoxyphenyl)-1,2,3-triazole
(13b): General procedure C was followed, starting with 3-methoxyaniline (16 mg, 0.13
mmol). The reaction mixture was stirred for 3 h and was purified by siliga gel column
chromatography (n-hexane/EtOAc 1:1) provided the product as a brown solid in 32% yield
23

1
(80.0 mg); Rf = 0.30 (n-hexane/EtOAc 7:13); [α] ꢀꢁ-21.5 (c 0.7, CHCl3 ); mp = 134-136 °C;
ꢂ
1
2
3
IR (film) 2922, 2852, 1744, 1603, 1457, 1367, 1213, 1034, 598 cm-1; H NMR (400 MHz,
CDCl3) δ 7.70 (s, 2H, H-triazole), 7.12 (t, 1H, J =8.0 Hz, H-Ar), 6.42 (dd, 1H, J =8.0, 2.0 Hz,
H-Ar), 6.38-6.31 (m, 2H, H-Ar), 5.85 (d, 2H, J = 9.2 Hz, H-1), 5.49 (t, 2H, J = 9.2 Hz, H-3),
5.40 (t, 2H, J = 9.2 Hz, H-4), 5.19 (t, 2H, J = 9.2 Hz, H-2), 4.66 (d, 4H, J = 5.2 Hz, H-3′),
4.25 (dd, 2H, J = 12.8, 4.8 Hz, H-6a), 4.14 (dd, 2H, J = 11.6, 1.5 Hz, H-6b), 3.98 (ddd, 2H, J
= 10.0, 4.8, 2.0 Hz, H-5), 3.73 (s, 3H, H-CH3), 2.06 (s, 6H, OAc), 2.05 (s, 6H, OAc), 2.02(s,
4
5
6
7
13
8
6H, OAc), 1.80 (s, 6H, OAc); C NMR (100 MHz, CDCl3) δ 170.48 (2C), 169.93 (2C),
9
169.27 (2C), 169.00 (2C), 160.74, 149.18, 146.35 (2C), 130.00, 120.60 (2C), 106.57, 103.45,
99.99, 85.72 (2C), 75.13 (2C), 72.60 (2C), 70.09 (2C), 67.71 (2C), 61.62 (2C), 55.09, 47.40
(2C), 20.65 (2C), 20.50 (2C), 20.45 (2C), 20.01 (2C); HRMS (ESI) m/z calcd for
C41H51N7O19 (M+H)+ 946.3318, found 946.3673.
10
11
12
13
14
15
16
di-1-(2,3,4,6-Tetra-O-acetyl-β-
D-glucopyranosyl)-4-(4-bromophenyl)-1,2,3-triazole
(13c): General procedure C was followed, starting with 4-bromoaniline (22.4 mg, 0.13 mmol)
The reaction mixture was stirred for 3 h and was purified by siliga gel column
chromatography (n-hexane/EtOAc 7:13) provided the product as a brown solid in 32% yield
17
(85.0 mg); Rf = 0.38 (n-hexane/EtOAc 7:13); [α] ꢀꢁ-18.5 (c 0.7, CHCl3 ); mp = 190-192 °C;
ꢂ
1
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
IR (film) 2923, 2852, 1743, 1594, 1498, 1367, 1216, 1036, 926, 598 cm-1; H NMR (400
MHz, CDCl3) δ 7.70 (s, 2H, H-triazole), 7.27 (d, 2H, J =8.4 Hz, H-Ar), 6.69 (d, 2H, J =8.4
Hz, H-Ar), 5.69 (d, 2H, J = 9.2 Hz, H-1), 5.48 (t, 2H, J = 9.2 Hz, H-3), 5.40 (t, 2H, J = 9.2
Hz, H-2), 5.18 (t, 2H, J = 9.6 Hz, H-4), 4.65 (d, 4H, J = 12.0 Hz, H-3′), 4.25 (dd, 2H, J =
12.8, 5.2 Hz, H-6a), 4.15 (dd, 2H, J = 11.6, 1.5 Hz, H-6b), 3.98 (ddd, 2H, J = 10.0, 5.2, 2.0
13
Hz, H-5), 2.06 (s, 6H, OAc), 2.05 (s, 6H, OAc), 2.02(s, 6H, OAc), 1.79 (s, 6H, OAc); C
NMR (100 MHz, CDCl3) δ 170.36 (2C), 169.77 (2C), 169.25 (2C), 168.77 (2C), 146.27 (2C),
131.86 (2C), 120.02 (2C), 114.68 (2C), 109.58 (2C), 85.56 (2C), 74.96 (2C), 72.47 (2C)
70.10 (2C), 67.59 (2C), 61.41 (2C), 39.57 (2C), 20.54 (2C), 20.41 (2C), 20.37 (2C), 19.93
(2C); HRMS (ESI) m/z calcd for C40H48BrN7O18 (M+H)+ 994.2317, found 994.2632.
Acknowledgments
This work was supported by a Research Grant from Burapha University through the
National Research Council of Thailand, The Research Unit in Synthetic Compounds and
Synthetic Analogues from Natural Product for Drug Discovery (RSND) and Center of
Excellence for Innovation in Chemistry (PERCH-CIC). R.S. and W.S. are grateful for the
24

1
2
3
4
Science Achievement Scholarship of Thailand (SAST) for their Ph.D. support. Special thanks
to Prof. Dr Frederick W. H. Beamish and Dr. Ronald Beckett, Faculty of Science, Burapha
University, for their comments and English corrections.
5
6
Supplementary data
Supplementary data associated with this article can be found, in the online version, at
7
8
References
9
[1]
Y. Yang, X. Zhang, B. Yu, O-Glycosylation methods in the total synthesis of complex
natural glycosides, Nat. Prod. Rep., 32 (2015) 1331- 1355.
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
[2]
K. Kitamura, Y. Ando, T. Matsumoto, K. Suzuki, Total Synthesis of Aryl C-
Glycoside Natural Products: Strategies and Tactics, Chem. Rev., 118 (2018) 1495-
1598.
[3]
S. S. Kulkarni, C. C. Wang, N. M. Sabbavarapu, A. R. Podilapu, P. H. Liao, S. C.
Hung, “One-Pot” Protection, Glycosylation, and Protection−Glycosylation Strategies
of Carbohydrates, Chem. Rev., 118 (2018) 8025-8104.
[4]
[5]
[6]
[7]
[8]
B. Yu, J. Sun, X. Yang Assembly of Naturally Occurring Glycosides Evolved Tactics,
and Glycosylation Methods, Acc. Chem. Res., 45 (2012) 1227-1236.
K. Toshima, K. Tatsuta, Recent Progress in O-Glycosylation Methods and Its
Application to Natural Products Synthesis, Chem. Rev., 93 (1993) 1503-1531.
C. S. Bennett, M. C. Galan, Methods for 2-Deoxyglycoside Synthesis, Chem. Rev.,
118 (2018) 7931-7985.
H. Y. Wang, S. A. Blaszczyk, G. Xiao, W. Tang, Chiral reagents in glycosylation and
modification of carbohydrates, Chem. Soc. Rev., 47 (2018) 681-701.
W. L. Leng, H. Yao, J. X. He, X. W. Liu, Venturing beyond Donor-Controlled
Glycosylation: New Perspectives toward Anomeric Selectivity, Acc. Chem. Res., 51
(2018) 628-639.
[9]
S. K. Jana, M. Löppenberg, C. G. Daniliuc, J. Jose, R. Holl, Development of novel
LpxC inhibitors: chiral-pool synthesis of C-triazolyl glycosides, Tetrahedron, 69
(2013) 9434-9442.
[10] B. Amit, U. Zehavi, A. Patchornik, Photosensitive Protecting Groups of Amino
Sugars and Their Use in Glycoside Synthesis. 2-Nitrobenzyloxycarbonylamino and 6-
Nitroveratryloxycarbonylamino Derivatives, J. Org. Chem., 39 (1974) 192-196.
25

1
2
[11] C. M. Klemm, A. Berthelmann, S. Neubacher, C. Arenz, Short and Efficient
Synthesis of Alkyne-Modified Amino Glycoside Building Blocks, Eur. J. Org. Chem.,
2009 (2009) 2788-2794.
3
4
[12] N. Thamban Chandrika, S. Garneau-Tsodikova, Comprehensive review of chemical
strategies for the preparation of new aminoglycosides and their biological activities,
Chem. Soc. Rev., 47 (2018) 1189-1249.
5
6
7
[13] G. Cox, L. Ejim, P. J. Stogios, K. Koteva, E. Bordeleau, E. Evdokimova, A. O.
Sieron, A. Savchenko, A. W. Serio, K. M. Krause, G. D. Wright, Plazomicin Retains
Antibiotic Activity against Most Aminoglycoside Modifying Enzymes, ACS. Infect.
Dis., 4 (2018) 980-987.
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
[14] D. Tadic, T. Welzel, P. Seidel, E. Wüst, E. Dingeldein, M. Epple, Controlled release
of gentamicin from biomimetic calcium phosphate in vitro. Comparison of four
different incorporation methods, Mat.-wiss. u. Werkstofftech., 35 (2004) 1001-1005.
[15] P. K. Govindappa, V. Gautam, S. M. Tripathi, Y. P. Sahni, H. L. S. Raghavendra,
Effect of Withania somnifera on gentamicin induced renal lesions in Rats, Rev. bras.
farmacogn., 29 (2019) 234-240.
[16] S. Bera, D. Mondal, S. Palit, F. Schweizer, Structural modifications of the neomycin
class of Aminoglycosides, Med. Chem. Comm., 7 (2016) 1499-1534.
[17] H. Prescher, A. Schweizer, E. Kuhfeldt, L. Nitschke, R. Brossmer, New Human
CD22/Siglec-2 Ligands with a Triazole Glycoside, Chembiochem, 18 (2017) 1216-
1225.
[18] K. T. Petrova, T. M. Potewar, P. Correia-da-Silva, M. T. Barros, R. C. Calhelha, A.
Ciric, M. Sokovic, I. C. Ferreira, Antimicrobial and cytotoxic activities of 1,2,3-
triazole-sucrose Derivatives, Carbohydr. Res., 417 (2015) 66-71.
[19] B. H. M. Kuijpers, S. Groothuys, A. R. Keereweer, P. J. L. M. Quaedflieg, R. H.
Blaauw, F. L. van Delft, F. P. J. T. Rutjes, Expedient Synthesis of Triazole-Linked
Glycosyl Amino Acids and Peptides, Org. Lett., 6 (2004) 3123-3126.
[20] B. L. Wilkinson, L. F. Bornaghi, T. A. Houston, A. Innocenti, D. Vullo, C. T.
Supuran, S. A. Poulsen, Carbonic Anhydrase Inhibitors: Inhibition of Isozymes I, II,
and IX with Triazole-Linked O-Glycosides of Benzene Sulfonamides, J. Med. Chem.,
50 (2007) 1651-1657.
[21] I. Mohammed, I. R. Kummetha, G. Singh, N. Sharova, G. Lichinchi, J. Dang, M.
Stevenson, T. M. Rana, 1,2,3-Triazoles as Amide Bioisosteres: Discovery of a New
Class of Potent HIV-1 Vif Antagonists, J. Med. Chem., 59 (2016) 7677-7682.
26

1
2
[22] S. Zhang, Z. Xu, C. Gao, Q. C. Ren, L. Chang, Z. S. Lv, L. S. Feng, Triazole
derivatives and their anti-tubercular activity, Eur. J. Med. Chem., 138 (2017) 501-513.
[23] X. M. Chu, C. Wang, W. L. Wang, L. L. Liang, W. Liu, K. K. Gong, K. L. Sun,
Triazole derivatives and their antiplasmodial and antimalarial activities, Eur. J. Med.
Chem., 166 (2019) 206-223.
3
4
5
6
[24] S. K. Maurya, D. R. Gollapalli, S. Kirubakaran, M. Zhang, C. R. Johnson, N. N.
Benjamin, L. Hedstrom, G. D. Cuny, Triazole Inhibitors of Cryptosporidium parvum
Inosine 50-Monophosphate Dehydrogenase, J. Med. Chem., 52 (2009) 4623-4630.
[25] S. Bai, S. Li, J. Xu, X. Peng, K. Sai, W. Chu, Z. Tu, C. Zeng, R. H. Mach, Synthesis
and Structure−Activity Relationship Studies of Conformationally Flexible
Tetrahydroisoquinolinyl Triazole Carboxamide and Triazole Substituted Benzamide
Analogues as σ2 Receptor Ligands, J. Med. Chem., 57 (2014) 4239-4251.
[26] H. C. Kolb, M. G. Finn, K. B. Sharpless, Click Chemistry: Diverse Chemical
Function from a Few Good Reactions, Angew. Chem. Int. Ed., 40 (2001) 2004-2021.
[27] K. Kitamura, Y. Ando, T. Matsumoto, K. Suzuki, Total Synthesis of Aryl C-
Glycoside Natural Products: Strategies and Tactics, Chem. Rev., 118 (2018) 1495-
1598.
7
8
9
10
11
12
13
14
15
16
17
18
19
20
[28] Z. Y. Yan, Y. B. Zhao, M. J. Fan, W.M. Liu, Y. M. Liang, General synthesis of (1-
substituted-1H-1,2,3-triazol-4-ylmethyl)-dialkylamines via a copper(I)-catalyzed
three-component reaction in water, Tetrahedron, 61 (2005) 9331-9337.
27