Phenyl 2-azido-2-deoxy-1-selenogalactosides: a single type of glycosyl donor for the highly stereoselective synthesis of α- and β-2-azido-2-deoxy-d-galactopyranosides

Article abstract of DOI:10.1016/j.tetlet.2016.01.013

Efficient glycosylation with phenyl 2-azido-2-deoxy-1-seleno-α-d-galactosides of glycosyl acceptors with different reactivities has been developed. The reaction provided glycosides of 2-azido-2-deoxy-d-galactose in good to high yields. The stereochemical outcome of the glycosylation of reactive acceptors (3-trifluoroacetamidopropanol and methyl 2,3-O-isopropylidene-α-l-rhamnopyranoside) can be broadly varied from complete β- to high α-selectivity by changing the reaction solvent, promoter and protecting groups in the donor, while the glycosylation of less reactive allyl 2,2′,3,3′,6,6′-hexa-O-benzoyl-β-lactoside afforded the corresponding α-glycosides exclusively.

Full text of DOI:10.1016/j.tetlet.2016.01.013

Tetrahedron Letters xxx (2016) xxx–xxx
Contents lists available at ScienceDirect
Tetrahedron Letters
journal homepage: www.elsevier.com/locate/tetlet
Phenyl 2-azido-2-deoxy-1-selenogalactosides: a single type
of glycosyl donor for the highly stereoselective synthesis of
b-2-azido-2-deoxy-D-galactopyranosides
a- and
⇑
Elena A. Khatuntseva, Andrey A. Sherman, Yury E. Tsvetkov, Nikolay E. Nifantiev
Laboratory of Glycoconjugate Chemistry, N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Prospect 47, 119991 Moscow, Russian Federation
a r t i c l e i n f o
a b s t r a c t
Article history:
Efficient glycosylation with phenyl 2-azido-2-deoxy-1-seleno-
different reactivities has been developed. The reaction provided glycosides of 2-azido-2-deoxy-
a
-
D
-galactosides of glycosyl acceptors with
-galac-
tose in good to high yields. The stereochemical outcome of the glycosylation of reactive acceptors (3-tri-
fluoroacetamidopropanol and methyl 2,3-O-isopropylidene- -rhamnopyranoside) can be broadly
varied from complete b- to high -selectivity by changing the reaction solvent, promoter and protecting
groups in the donor, while the glycosylation of less reactive allyl 2,20,3,30,6,60-hexa-O-benzoyl-b-lactoside
afforded the corresponding -glycosides exclusively.
Received 15 November 2015
Revised 4 January 2016
Accepted 6 January 2016
Available online xxxx
D
a
-L
a
Keywords:
Galactosamine
2-Azido-2-deoxygalactose
2-Azido-2-deoxy-1-selenogalactosides
Glycosylation
a
Ó 2016 Elsevier Ltd. All rights reserved.
Stereoselectivity
Introduction
for the indirect application of 2-azido-2-deoxyselenogalactosides,
that is, involving their prior transformation to more conventional
2-azido-2-deoxygalactosyl fluoride10 or imidates,9,11 in oligosac-
charide synthesis. However, to the best of our knowledge, neither
the direct application of 2-azido-2-deoxyselenogalactosides to
the synthesis of GalN-containing oligosaccharides, nor the system-
atic study of factors affecting the efficiency and stereoselectivity of
glycosylation by these donors has been reported thus far. Mean-
while, it would be very attractive to use a single type of glycosyl
donors, which, in addition, can be efficiently obtained in one step
N-Acetyl-D-galactosamine (GalNAc) is widely distributed in liv-
ing systems being a principal constituent of glycoproteins, glycol-
ipids, proteoglycans,1 and polysaccharides of bacterial2 and
fungal3 origin. In these glycoconjugates, GalNAc can be bound to
other monosaccharides (or to amino acids) by both
coside bonds. -Galactosamine is commercially available but
a- and b-gly-
D
rather expensive; for this reason, derivatives of 2-azido-2-deoxy-
galactose are usually used in the synthesis of GalNAc-containing
oligosaccharides or O-glycosylated amino acids. Most often, 2-
azido-2-deoxygalactosyl donors are synthesized by azidonitration
from available D-galactal, for both stereoselective a- and b-glycosy-
lation depending on the reaction conditions and/or protecting
group pattern in the donor. In this communication, we report the
results of our search for optimal conditions allowing the stereose-
of D
-galactal according to the Lemieux procedure4 and subsequent
transformation of the formed 2-azido-2-deoxygalactosyl nitrates
over several synthetic steps into the corresponding 2-azido-2-
deoxygalactosyl halides, imidates, and other types of glycosyl
donors. Recently we reported an improved method for the homo-
lective synthesis of
a- and b-glycosides of 2-azido-2-deoxygalac-
tose with different glycosyl acceptors from phenyl 2-azido-2-
deoxy-1-selenogalactosides.
geneous azidophenylselenylation of D-galactal derivatives leading
in one step to phenyl 2-azido-2-deoxyselenogalactosides5 that
can be directly used as 2-azido-2-deoxygalactosyl donors. Thus,
some phenyl 2-azido-2-deoxyselenogalactosides were employed
Results and discussion
Glycosylation with fully acetylated and benzoylated selenogly-
cosides 15 and 2 (obtained by conventional deacetylation of 1 fol-
lowed by benzoylation), and 4,6-O-benzylidene-protected donor 39
was examined. In the first step, 3-trifluoroacetamidopropanol 4, a
reactive primary alkanol often used for the introduction of a 3-
aminopropyl spacer group in oligosaccharides of different types,12
for the
a-glycosylation of L-serine and L
-threonine derivatives6,7
and simple aliphatic alcohols.6,8,9 Also, few examples are known
⇑
Corresponding author. Tel./fax: +7 499 135 8784.
E-mail address: nen@ioc.ac.ru (N.E. Nifantiev).
http://dx.doi.org/10.1016/j.tetlet.2016.01.013
0040-4039/Ó 2016 Elsevier Ltd. All rights reserved.
Please cite this article in press as: Khatuntseva, E. A.; et al. Tetrahedron Lett. (2016), http://dx.doi.org/10.1016/j.tetlet.2016.01.013

2
E. A. Khatuntseva et al. / Tetrahedron Letters xxx (2016) xxx–xxx
Table 1
was chosen as a glycosyl acceptor (Scheme 1). Generally, most of
the glycosyl donors and promoter systems were tested in three sol-
vents: ‘neutral’ dichloromethane to reveal the intrinsic stereoselec-
tivity of a certain donor—acceptor—promoter combination, diethyl
Glycosylation of 3-trifluoroacetamidopropanol 4 by donors 1–3
Entry Donor Promoter Solvent Temperature
Product
(s)
Ratioa
(total
a:b
(°C)
yield %)b
ether which favors
a
-selectivity,13 and acetonitrile which facili-
tates the formation of b-glycosides.14 The results are presented in
Table 1. Modulation of the glycosylation stereoselectivity by per-
forming the reactions in the presence of various nucleophilic15a,b
or complexing15c additives was not studied in this work.
1
2
1
1
1
1
1
1
2
2
2
2
2
3
3
NIS,
TfOH
NIS,
TfOH
NIS,
TfOH
NIS,
TfOH
NIS,
TfOH
NIS,
TfOH
NIS,
TfOH
NIS,
CH2Cl2
Et2O
–35
20
5, 6
5, 6
5, 6
5, 6
5, 6
6
1:2 (88)
1:1 (95)
1:1 (95)
1:3 (95)
1:10 (95)
3
Et2O
0
(NIS–TfOH)-promoted glycosylation of 4 with acetylated donor
1 afforded an anomeric mixture of glycosides 5 and 6 in high yield
with a slight predominance of the b-anomer (entry 1). The same
4
Et2O
–35
–78
–35
–35
–35
–35
0
5
Et2O
reaction in diethyl ether demonstrated no increase in a-selectivity
but pronounced temperature dependence (entries 2–5). Lowering
the temperature resulted in better b-selectivity, which achieved a
rather high value of 1:10 at ꢀ78 °C (entry 5). The observed temper-
ature effect is in agreement with the published data.16 The reaction
in acetonitrile displayed the highest b-selectivity providing b-
linked glycoside 6 exclusively (entry 6).
(NIS–TfOH)-promoted glycosylation with perbenzoylated donor
2 produced a mixture of glycosides 7 and 8 with a somewhat
higher proportion of the a-product as compared to the acetylated
counterpart 1 (cf. entries 1 and 7; 4 and 8) that may be explained
by more effective remote anchimeric participation17 of the benzoyl
groups in comparison to the acetyl ones.18 Otherwise, the stereo-
chemical results obtained with glycosyl donor 2, including the sol-
vent effects (entries 8, 9), were similar to those with 1. Application
of the promoter system PhSeCl–AgOTf19 allowed for further
6
MeCN
CH2Cl2
Et2O
Only b
(88)
1:1 (92)
7
7, 8
7, 8
8
8
1:1.3 (78)
TfOH
NIS,
9
MeCN
CH2Cl2
Et2O
Only b
(75)
2.4:1 (95)
TfOH
PhSeCl,
AgOTf,
PhSeCl,
AgOTf
NIS,
10
11
12
13
7, 8
7, 8
9, 10
9, 10
0
3.3:1 (95)
1:1.5 (95)
1:1.6 (91)
Et2O
–35
20
TfOH
MeOTf
CH2Cl2
a
Anomeric ratios were calculated from the 1H NMR spectra of isolated mixtures
- and b-anomers by integration of their characteristic signals (see Supple-
mentary Data).
of
a
enhancement of
AgOTf)-promoted glycosylation in diethyl ether (entry 11) may
certainly be regarded as a preparative route to -glycoside 7 and
similar alkyl -glycosides.
a-selectivity (entries 10, 11). Thus, (PhSeCl–
b
Isolated yields.
a
rhamnoside 11 in dichloromethane was slightly b-stereoselective
and produced a mixture of disaccharide 12 and 13 in a ratio of
1:1.7 (Table 2, entry 1). The observed stereoselectivity was very
close to that in the glycosylation of acceptor 4 under the same con-
ditions (cf. Table 1, entry 1). b-Selectivity for the glycosylation of
11 could be considerably improved by lowering the reactant con-
centration22 (entry 2), however, the overall efficiency of the reac-
tion decreased. The same rather high b-selectivity was observed
for the glycosylation of 11 in acetonitrile (entry 5). Conversely,
the use of diethyl ether as the reaction solvent resulted in predom-
inant formation of
moted glycosylation of 11 with 1 in dichloromethane produced
somewhat more -disaccharide 12 than the same (NIS–TfOH)-pro-
moted reaction (cf. entries 1 and 6). As expected, [NIS–Bi(OTf)3]-
promoted coupling of 1 and 11 in acetonitrile provided good b-
selectivity, however, at the expense of the total glycosylation effi-
ciency (entry 7). The use of an inverse order of reagent mixing con-
sisting of adding the donor to a solution of the acceptor and
a
4,6-O-Benzylidene-protected donor 3 was also examined. It is
known20 that the replacement of acyl groups at O-4 and O-6 by a
benzylidene acetal enhances the reactivity of the glycosyl donor.
However, it turned out that the increase in the donor reactivity
did not affect glycosylation stereoselectivity. Thus, (NIS–TfOH)-
promoted glycosylation with 3 in diethyl ether demonstrated
almost the same stereochemical result as that observed for ben-
zoylated counterpart 2 (cf. entries 7 and 12). Application of less
reactive methyl triflate as the promoter, which might provide a
higher proportion of 1,2-cis-product,21 for glycosylation with 3
did not show any noticeable changes in stereoselectivity (entry
13).
a-product 12 (entry 4). [NIS–Bi(OTf)3]-pro-
a
Thus, glycosylation of the reactive primary alcohol with phenyl
2-azido-2-deoxyselenogalactosides features intrinsic b-selectivity
and becomes b-stereospecific in acetonitrile. Nevertheless, reaction
conditions providing good
(PhSeCl–AgOTf, Et2O) making these donors applicable for the prac-
tical stereoselective synthesis of both - and b-2-azido-2-deoxy-
a-selectivity have been also found
promoter allowed a two-fold increase in
a-selectivity (entries 3,
a
8) compared to the conventional procedure, that is, addition of
the promoter to a mixture of the donor and acceptor, but slightly
decreased the total yield of glycosylation products.
galactosides from reactive primary alcohols.
Then, glycosylation of methyl 2,3-O-isopropylidene-a-L-
rhamnopyranoside 11 was studied (Scheme 2). This acceptor is
As had occurred in the case of glycosylation of acceptor 4, appli-
cation of benzoylated donor 2 provided a higher proportion of the
often used in model glycosylations as a reactive secondary sugar
alcohol.13 (NIS–TfOH)-promoted coupling of donor
1
and
a-disaccharide (entry 9). Further increase in a-selectivity was
OR3
O
OR3
O
OR3
O
R2O
R1O
R2O
R1O
R2O
R1O
O
NHCOCF3
HO
NHCOCF3
+
+
N
N
N3
3SePh
3O
NHCOCF3
4
1 R1 = R2 = R3 = Ac
2 R1 = R2 = R3 = Bz
5 R1 = R2 = R3 = Ac
7 R1 = R2 = R3 = Bz
6 R1 = R2 = R3 = Ac
8 R1 = R2 = R3 = Bz
3 R1 = Ac, R2 + R3 = PhCH<
9 R1 = Ac, R2 + R3 = PhCH<
10 R1 = Ac, R2 + R3 = PhCH<
Scheme 1.
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E. A. Khatuntseva et al. / Tetrahedron Letters xxx (2016) xxx–xxx
3
OR3
O
OR3
O
OMe
R2
R1O
O
R2O
R1O
OR3
O
R2O
OMe
OMe
O
HO
+
+
O
R1O
O
O
N
O
N
O
3O
3SePh
O
N3
O
O
O
11
1 R1 = R2 = R3 = Ac
2 R1 = R2 = R3 = Bz
12 R1 = R2 = R3 = Ac
14 R1 = R2 = R3 = Bz
13 R1 = R2 = R3 = Ac
15 R1 = R2 = R3 = Bz
3 R1 = Ac, R2 + R3 = PhCH<
16 R1 = Ac, R2 + R3 = PhCH<
17 R1 = Ac, R2 + R3 = PhCH<
Scheme 2.
OBz
O
Table 2
Glycosylation of methyl 2,3-O-isopropylidene-
1–3
OR3
O
R2O
R1O
OBz
a
-L-rhamnopyranoside 11 by donors
BzO
HO
O
OAll
+
BzO
O
OBz
N
3SePh
18
Entry Donor Promoter Solvent Temperature
Products Ratioc
(total
a:b
OBz
2 R1 = R2 = R3 = Bz
3 R1 = Ac, R2 + R3 = PhCH<
(°C)
yield %)d
OR3
R2O
1
2
1
1
1
1
1
1
1
1
2
2
2
2
2
2
3
3
NIS,
CH2Cl2
CH2Cl2
CH2Cl2
Et2O
ꢀ35
ꢀ35
ꢀ35
ꢀ35
ꢀ35
ꢀ10
ꢀ10
ꢀ10
ꢀ35
ꢀ35
ꢀ35
ꢀ10
0
12, 13
12, 13
12, 13
12, 13
12, 13
12, 13
12, 13
12, 13
14, 15
14, 15
14, 15
14, 15
14, 15
14, 15
16, 17
16, 17
1:1.7 (80)
TfOH
NIS,
O
R1O
1:6 (63)
TfOHa
NIS,
N
3O
OBz
O
OBz
3
2:1 (50)
BzO
OAll
TfOHb
NIS,
BzO
O
O
OBz
4
3.5:1 (87)
1:6 (70)
OBz
TfOH
NIS,
19 R1 = R2 = R3 = Bz
5
CH3CN
CH2Cl2
CH3CN
CH2Cl2
CH2Cl2
Et2O
20 R1 = Ac, R2 + R3 = PhCH<
TfOH
NIS, Bi
(OTf)3
NIS, Bi
(OTf)3
NIS, Bi
(OTf)3
NIS,
TfOH
NIS,
TfOH
NIS,
TfOH
NIS, Bi
(OTf)3
PhSeCl,
AgOTf
PhSeCl,
AgOTf
NIS,
6
1.2:1 (75)
1:8 (53)
Scheme 3.
7
8
2.7:1 (61)
2.5:1 (80)
3.6:1 (88)
1:3.8 (80)
7:1 (63)
Table 3
Glycosylation of allyl 2,20,3,30,6,60-hexa-O-benzoyl-b-lactoside 18 by donors 2 and 3
b
9
Entry Donor Promoter Solvent
Temperature
Product Isolated
yield (%)
10
11
12
13
14
15
16
(°C)
1
2
NIS,
Et2O–
CH2Cl2
(2:1)
–35
19
74
CH3CN
CH2Cl2
CH2Cl2
Et2O
TfOH
b
2
3
3
3
NIS,
Et2O
–35
20
20
20
80
64
TfOH
MeOTf
3:1 (72)
Et2O–
CH2Cl2
(2:1)
0
4.7:1 (99)
2.2:1 (72)
3:1 (79)
Et2O
ꢀ35
20
TfOH
MeOTf
CH2Cl2
slightly enhanced the
16).
a-stereoselectivity of glycosylation (entry
a
b
c
5-Fold dilution.
Inverse order of reagent mixing.
Anomeric ratios were calculated from the 1H NMR spectra of isolated mixtures
- and b-anomers by integration of their characteristic signals (see Supple-
mentary Data).
In comparison to the glycosylation of primary acceptor 4, glyco-
sylation of the less reactive secondary acceptor 11 generally tends
to form a higher proportion of 2-azido-2-deoxy-a-galactosides (for
example, cf. entries 4, 7, 8 in Table 1 and entries 4, 9, 10 in Table 2).
This is in agreement with the existing concept of increasing 1,2-cis-
stereoselectivity upon decreasing acceptor reactivity.13a,21
However, good b-selectivity is also achievable under certain
conditions, for example, when the glycosylation is carried out in
acetonitrile or at a lower concentration (entries 2, 5, 11).
of
a
d
Isolated yields.
achieved when the reaction was carried out in diethyl ether (entry
10), whereas the use of acetonitrile as the reaction solvent
switched the stereoselectivity (entry 11). The highest
a-stereose-
Finally, we studied the 40-O-glycosylation of hexabenzoylated
allyl lactoside 1823 as a representative of less reactive acceptor
(Scheme 3). The axial hydroxyl group at C-4 in the galactose resi-
due is considered to be low reactive in itself; additionally, its reac-
tivity is reduced by the presence of neighboring benzoyl protecting
groups.13a,21 It turned out that glycosylation in diethyl ether or in
an ether–dichloromethane mixture (for better solubility of 18)
lectivity in dichloromethane was observed when the inverse pro-
cedure was applied to the [NIS–Bi(OTf)3]-promoted reaction of
compounds 2 and 11 (entry 12), but again the total yield of the gly-
cosylation products 13 and 14 decreased. The (PhSeCl–AgOTf)-pro-
moted coupling of 2 to 11 in dichloromethane demonstrated good
intrinsic
a-stereoselectivity (entry 13); the best result in terms of
both efficiency and
a
-stereoselectivity was achieved when this gly-
cosylation was performed in diethyl ether (entry 14).
exclusively provided
donor structure and the promoter system (Table 3). An attempt
to accomplish (NIS–TfOH)-promoted b-stereoselective
a-products 19 or 20 irrespective of the
Donor 3 in the (NIS–TfOH)-promoted glycosylation of 11 in
diethyl ether demonstrated somewhat lower
a-selectivity than
acylated donors 1 and 2 under the same conditions (cf. entries
glycosylation of 18 with 2 by performing it in acetonitrile failed;
15 and 4, 10). The use of methyl triflate as the promoter only
no formation of the expected glycosides was detected.
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4
E. A. Khatuntseva et al. / Tetrahedron Letters xxx (2016) xxx–xxx
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of different reactivity. Glycosylation stereoselectivity can be varied
from complete b-selectivity to high
a-selectivity by changing the
reaction solvent, promoter and protecting group pattern in the gly-
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generally provides high b-stereoselectivity, while a-glycoside for-
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are promoted with PhSeCl–AgOTf. The acceptor of low reactivity,
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lation reaction to the synthesis of biologically relevant
oligosaccharides is now in progress in this laboratory and will be
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Acknowledgment
This work was supported by the Russian Science Foundation
(grant no. 14-50-00126).
Supplementary data
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Please cite this article in press as: Khatuntseva, E. A.; et al. Tetrahedron Lett. (2016), http://dx.doi.org/10.1016/j.tetlet.2016.01.013