Syntheses and characterization of new 3-O-allyl ether chloralose derivatives

Article abstract of DOI:10.14233/ajchem.2015.17975

The new 3-O-allyl ether derivatives of sugar were synthesized with high yield and mild reaction conditions. The synthesis of 3-O-acetylchloralose derivatives (5-8) and 3-O-allyl ether chloralose derivatives (9-12) were carried out. These new 3-O-allyl eth

Full text of DOI:10.14233/ajchem.2015.17975

Asian Journal of Chemistry; Vol. 27, No. 1 (2015), 353-356
ASIAN JOURNAL OF CHEMISTRY
http://dx.doi.org/10.14233/ajchem.2015.17975
Syntheses and Characterization of New 3-O-Allyl Ether Chloralose Derivatives
FATMA ÇETIN TELLI
Department of Chemistry, Faculty of Science, Ege University, Bornova 35100, Izmir, Turkey
Corresponding author: Tel/Fax: +90 232 3888264; E-mail: fatma.cetin@ege.edu.tr
Received: 9 May 2014;
Accepted: 2 December 2014;
Published online: 26 December 2014;
AJC-16570
The new 3-O-allyl ether derivatives of sugar were synthesized with high yield and mild reaction conditions. The synthesis of 3-O-
acetylchloralose derivatives (5-8) and 3-O-allyl ether chloralose derivatives (9-12) were carried out. These new 3-O-allyl ether of chloralose
derivatives are potential monomers for the synthesis of new glycopolymers.
Keywords: Allyl ethers, Chloralose, Furano sugars, Glycomonomers.
as biodegradability, biocompatibility and biorenewability can
be achieved14 and so this could be avaiable alternative for deve-
lophing environmental friendly products. Some applications
of sugar-carrying polymers are drug delivery systems, dental
medicine, bioimplants, contect lenses, tissue engineering and
many medicinal applications15. Additionally, they have the
advantage of being potentionally biodegradable. For example,
sugar-containing vinyl monomers were synthesized from
INTRODUCTION
The allyl group is widely used in carbohydrate chemistry.
It survives a variety of reaction conditions (acidic or basic)
that permits orthogonal protection strategies and can be selec-
tively removed1. Fedorynski et al.2 and Jarosz & Szewczyk3
protected the primary position by selective monoallylation and
were used in perparation of 6-O-allyl-3-O-benzyl-1,2-
isopropylidene-α-D-allofuranose. Sugar-carrying allylic ethers
such as 3-O-allyl-1,2,5,6-di-O-iso-propylidine-α-D-gluco-
furanose has already been reported4. Sugar-derived allylic
ethers were also converted into new glyco-substances having
isoxazolidine ring systems through intramolecular nitrone
addition reactions5. Furthermore, the allylic double bond can
be polymerized by free radical polymerization.
isopropylidene16 and other protected sugars14,17
.
EXPERIMENTAL
NMR spectra were recorded at 400 MHz (1H) and at 100.57
(13C) on a Varian Mercury FT NMR spectrometer at 300 K.
FTIR spectra were recorded on aVarian 670-IR spectrometer.
Chemical shift values (δ) are reported in ppm dowland field
from TMS as an international standard: J values are given Hz.
Elemental analyses (C,H) were performed with a Perkin-Elmer
series II 2400 analyse. Optical rotations were determined using
a Rudolph Research Analytical Autopol I automatic polari-
meter. TLC and column chromatography were performed on
precoated aluminium plates (Merck 5554) and silica gel G-60
(Merck 7734), respectively. Allyl alcohol, acetic anhydride
(Ac2O) and all the solvents were commercially obtained as
chemical pure reagents and used without purification. All
solvents were dried over moleculer sieves, for at least 2 h prior
to use. When dry conditions were required, the reaction was
performed under an argon atmosphere. All solvent removals
were carried out under reduced pressure. Light petroleum
refers to the fraction with b.pt. 40-70 °C. Petoleum ether :
EtOAc (7:3) was used for TLC. The spots on the TLC were
visualized using ethanolic solution of H2SO4 (5 %) followed
by heating at 110 °C for 5 min.
Allyl glycosides are often used as intermediate products
in the synthesis of oligosaccharides, in which the allyl group
may serve as an orthogonal protection group for the anomeric
center6,7. For example, Liu et al.8 and Khamsi et al.9 reported
some allyl glycosides form peracetylated glycosyl donors with
high yields10. The double bond of allyl glycosides has also
been utilized as a handle to functionalize carbohydrates for
generating glycoconjugates11. Additionally, the allylic double
bond can be modified by radical addition of thiols which allows
for further functionalization and derivization at the amino or
hydroxyl group12,13
.
Recently, the basic raw materials used for polymers have
expanded by including sugar such as glucose, galactose, fruc-
tose and sucrose. Chemically containing sugar moieties onto
synthetic polymers are individual method for functionalization
of synthetic polymers. Owing to this method, the polymer is
not only functionalized, but also other desirable properties such

354 Telli
Asian J. Chem.
General procedure for acetylation reaction: Firstly, a
FTIR (KBr, νmax, cm-1): 2984-2891 (C-H), 1709 (C=O), 1151
(COC), 798 (CH-Cl). 1H NMR (CDCl3, 400 MHz): δ 5.94 (d,
1H, J1,2 4.0 Hz, H-1), 5.64 (s, 1H, HCCl3), 5.10 (d, 1H, H-2),
4.12 (dd, 1H, J4,5 2.8 Hz, H-4), 4.43 (m, 1H, H-5), 4.28 (d,
1H, J3,4 3.2 Hz, H-3), 4.12 (dd, 1H, J6a,6b 8.0, J5,6a 6.0 Hz, H-6a),
3.94 (dd, J5,6b 5.6 Hz, H-6b), 2.09 (s, 3H, OAc), 1.41 (s, 3H,
CH3-isop.), 1.37 (s, 3H, CH3-isop.). 13C NMR: 169.5 (C=O),
115.7 (Cisop.), 107.7, 106.7 (HC-CCl3, C-1), 97.4 (HC-CCl3),
83.9, 83.4, 82.4 (C-2, C-3, C-4), 74.3 (C-5), 69.3 (C-6), 28.2,
27.5, 22.5. (Me groups).Anal. Calcd for C13H17O7Cl3: C, 39.87;
H, 4.38; found: C, 40.08; H, 4.19.
solution of 1,2-O-isopropylidene chloralose derivatives (1-4)
(3.50 g, 0.01 mol), Ac2O (6.6 mL, 0.07 mol) and 4-dimethyl-
aminopyridine (DMAP) (0.12 g, 0.001 mol) in dry pyridine:
EtOAc (1:10) (8:80 mL) was stirred for 24 h at room tempe-
rature under argon gas. A solution of reaction mixture was
extracted with 5% HCl solution (3 × 50 mL). Then the water
phase was extracted with EtOAc (3 × 100 mL). Organic phase
was dried over anhydrous Na2SO4, filtered off and evaporated
under reducing pressure. The residue was purified by column
chromatography with eluting solvent (light petroleum: EtOAc)
(6:4) to give pure 3-O-acetyl-1,2-O-isopropylidene chloralose
derivatives (5-8).
General procedure for etherification reaction: Firstly,
a solution of 3-O-acetyl-1,2-O-isopropylidene chloralose
derivatives (5-8) (3.92 g, 0.01 mol), allyl alcohol (0.82 mL,
0.012 mol) and boron trifluoride diethyl etherate (BF3.OEt2)
(4.73 mL, 0.05 mol) in dry acetonitrile (100 mL) was stirred for
2 to 5 h at 0 °C under argon gase. A solution was neutralized
with saturated solution of Na2CO3 and the solvent at 50 °C.
Then the water phase was extracted with EtOAc (3 × 100 mL).
Organic phase was dried over anhydrous Na2SO4, filtered off
and evaporated under reducing pressure. The residue was
purified by column chromatography with eluting solvent (light
petroleum: EtOAc) (9:1) to give pure 3-O-allyl-1,2-O-isopro-
pylidene chloralose derivatives (9-12).
3-O-Acetyl-5,6-O-isopropylidene-1,2-O-(R)-trichloro-
ethylidene-α-D-glucofuranose (5): The title product was
synthesized, yield 85 % (3.32 g). [α]20D -22.0 (c 1, CH2Cl2).
FTIR (KBr, νmax, cm-1): 2983-2895 (C-H), 1710 (C=O), 1148
(COC), 797 (CH-Cl). 1H NMR (CDCl3, 400 MHz): δ 6.10 (d,
1H, J1,2 3.6 Hz, H-1), 5.31 (s, 1H, HCCl3), 4.75 (d, 1H, H-2),
4.60 (ddd, 1H, H-5), 4.44 (dd, 1H, J4,5 2.8 Hz, H-4), 4.30 (d,
1H, J3,4 3.2 Hz, H-3), 4.16 (dd, 1H, J6a,6b 8.8, J5,6a 6.4 Hz, H-6a),
3.96 (dd, J5,6b 5.2 Hz, H-6b), 2.01(s, 3H, OAc), 1.40 (s, 3H,
CH3-isop.), 1.35 (s, 3H, CH3-isop.); 13C NMR: 169.5 (C=O),
115.7 (Cisop.), 109.7, 107.7 (HC-CCl3, C-1), 97.4 (HC-CCl3),
83.9, 83.4, 82.4 (C-2, C-3, C-4), 74.2 (C-5), 64.3 (C-6), 28.2,
27.5, 23.0 (Me groups).Anal. Calcd for C13H17O7Cl3: C, 39.87;
H, 4.38; found: C, 39.92; H, 4.04.
3-O-Allyl-5,6-O-isopropylidene-1,2-O-(R)-trichloro-
ethylidene-α-D-glucofuranose (9): The title product was
synthesized, yield 74 % (2.90 g). [α]21D -19.0 (c 1, CH2Cl2).
FTIR (KBr, νmax, cm-1): 2984-2895 (C-H), 1617 (C=C), 1152
(COC), 797 (CH-Cl). 1H NMR (CDCl3, 400 MHz): δ 6.05 (d,
1H, J1,2 3.6 Hz, H-1), 5.82 (m, 1H, CH2CH=CH2), 5.60 (s, 1H,
HCCl3), 5.25 (dd, 1H, CH2CH=CH2, J = 17.0, 1.4 Hz), 5.20
(dd, 1H, CH2CH=CH2, J = 10.3, 1.5 Hz), 4.73 (d, 1H, H-2),
4.65 (m, 1H, H-5), 4.47 (dd, 1H, J4,5 1.8 Hz, H-4), 4.25 (d,
1H, J3,4 3.2 Hz, H-3), 4.20 (m, 2H, OCH2CH=CH2), 4.14 (dd,
1H, J6a,6b 9.0, J5,6a 6.4 Hz, H-6a), 3.98 (dd, J5,6b 5.2 Hz, H-6b),
1.39 (s, 3H, CH3-isop.), 1.33 (s, 3H, CH3-isop.); 13C NMR:
133.3, 117.7 (CH=CH2), 115.1 (Cisop.), 108.1, 105.3 (HC-CCl3,
C-1), 99.3 (HC-CCl3), 86.1, 83.4, 79.4 (C-2, C-3, C-4), 71.9
(C-5), 68.5 (C-6), 29.2, 27.5, 22.9 (Me groups). Anal. Calcd
for C14H19O6Cl3: C, 43.12; H, 4.88; found: C, 42.72; H, 4.90.
3-O-Allyl-5,6-O-isopropylidene-1,2-O-(S)-trichloro-
ethylidene-α-D-glucofuranose (10): The title product was
synthesized, yield 68 % (2.65 g). [α]19D -12.0 (c 1.0, CH2Cl2).
FTIR (KBr, νmax, cm-1): 2980-2895 (C-H), 1611 (C=C), 1150
(COC), 796 (CH-Cl). 1H NMR (CDCl3, 400 MHz): 6.19 (d, 1H,
J1,2 = 3.6 Hz, H-1), 5.91 (s, 1H, HCCCl3), 5.80 (m, 1H,
CH2CH=CH2), 5.40 (dd, 1H, CH2CH=CH2, J = 17.2, 1.5 Hz),
5.27 (dd, 1H, CH2CH=CH2, J = 10.5, 1.3 Hz), 5.22 (d, 1H,
CH2CH=CH2), 4.70 (d, 1H, H-2), 4.31 (m, 1H, H-5), 4.10 (d,
1H, J3,4 = 6.0 Hz, H-3), 4.08 (dd, 1H, J4,5 = 2.7 Hz, H-4), 4.02
(m, 2H, OCH2CH=CH2), 3.95 (dd, 1H, J6a,6b = 9.6, J5,6a = 6.4 Hz,
H-6a), 3.80 (dd, 1H, J5,6b = 5.9 Hz, H-6b), 1.43 (s, 3H, CH3-
isopropylidene), 1.35 (s, 3H, CH3-isopropylidene). 13C NMR:
133.4, 117.6 (CH=CH2), 115.2 (Cisop.), 110.0, 107.6 (HC-CCl3,
C-1), 99.4 (HC-CCl3), 88.4, 84.3, 75.4 (C-2, C-3, C-4), 72.4 (C-
5), 68.8 (C-6), 27.3, 23.1, 20.5 (Me groups). Anal. Calcd for
C14H19O6Cl3: C, 43.12; H, 4.88; found: C, 42.88; H, 4.95.
3-O-Allyl-5,6-O-isopropylidene-1,2-O-(S)-trichloro-
ethylidene-α-D-galactofuranose (11): The title product was
3-O-Acetyl-5,6-O-isopropylidene-1,2-O-(S)-trichloro-
ethylidene-α-D-glucofuranose (6): The title product was
synthesized, yield 80 % (3.13 g). [α]21D -18.0 (c 0.96, CH2Cl2).
FTIR (KBr, νmax, cm-1): 2985-2892 (C-H), 1711 (C=O), 1150
(COC), 798 (CH-Cl). 1H NMR (CDCl3, 400 MHz): δ 6.17 (d,
1H, J1,2 = 3.9 Hz, H-1), 5.90 (s, 1H, HCCCl3), 4.72 (d, 1H,
H-2), 4.24 (ddd, 1H, H-5), 4.10 (d, 1H, J3,4 = 6.6 Hz, H-3),
4.08 (dd, 1H, J4,5 = 2.7 Hz, H-4), 3.95 (dd, 1H, J6a,6b = 9.7, J5,6a
= 6.4 Hz, H-6a), 3.80 (dd, 1H, J5,6b = 5.9 Hz, H-6b), 1.99 (s,
3H, OAc), 1.35 (s, 3H, CH3-isopropylidene), 1.21 (s, 3H, CH3-
isopropylidene.); 13C NMR: 169.2 (C=O), 115.3 (Cisop.), 110.0,
107.6 (HC-CCl3, C-1), 99.4 (HC-CCl3), 85.8, 82.7, 78.4 (C-2,
C-3, C-4), 75.6 (C-5), 67.2 (C-6), 28.7, 27.6, 23.1 (Me groups).
Anal. Calcd for C13H17O7Cl3: C, 39.87; H, 4.38; found: C,
39.62; H, 4.15.
3-O-Acetyl-5,6-O-isopropylidene-1,2-O-(S)-trichloro-
ethylidene-α-D-galactofuranose (7): The title product was
synthesized, yield 84 % (3.30 g). [α]20D -26.0 (c 1, CH2Cl2).
FTIR (KBr, νmax, cm-1): 2980-2891 (C-H), 1710 (C=O), 1153
(COC), 796 (CH-Cl). 1H NMR (CDCl3, 400 MHz): δ 6.21 (d,
1H, J1,2 4.0 Hz, H-1), 5.66 (s, 1H, HCCl3), 4.96 (d, 1H, H-2),
4.48 (dd, 1H, J4,5 2.8 Hz, H-4), 4.30 (d, 1H, J3,4 3.2 Hz, H-3),
4.18 (m, 1H, H-5), 4.10 (dd, 1H, J6a,6b 8.0, J5,6a 6.0 Hz, H-6a),
3.96 (dd, J5,6b 5.0 Hz, H-6b), 2.05 (s, 3H, OAc), 1.37 (s, 3H,
CH3-isop.), 1.29 (s, 3H, CH3-isop.). 13C NMR: 169.3 (C=O),
115.1 (Cisop.), 109.8, 107.6 (HC-CCl3, C-1), 98.4 (HC-CCl3),
84.8, 83.5, 82.7 (C-2, C-3, C-4), 79.8 (C-5), 67.3 (C-6), 25.5,
23.7, 21.0 (Me groups).Anal. Calcd for C13H17O7Cl3: C, 39.87;
H, 4.38; found: C, 39.90; H, 4.14.
3-O-Acetyl-5,6-O-isopropylidene-1,2-O-(R)-trichloro-
ethylidene-β-D-mannofuranose (8): The title product was
synthesized, yield 78 % (3.05 g). [α]20D -32.0 (c 1, CH2Cl2).

Vol. 27, No. 1 (2015)
Syntheses and Characterization of New 3-O-Allyl Ether Chloralose Derivatives 355
synthesized, yield 64 % (2.50 g). [α]21D -16.0 (c 1, CH2Cl2).
FTIR (KBr, νmax, cm-1): 2986-2890 (C-H), 1620 (C=C), 1149
(COC), 796 (CH-Cl). 1H NMR (CDCl3, 400 MHz): δ 6.21 (d,
1H, J1,2 4.0 Hz, H-1), 5.88 (m, 1H, CH2CH=CH2), 5.66 (s, 1H,
HCCl3), 5.22 (dd, 1H, CH2CH=CH2, J = 17.1, 1.4 Hz), 5.12
(dd, 1H, CH2CH=CH2, , J = 10.4, 1.3 Hz), 4.96 (d, 1H, H-2),
4.48 (dd, 1H, J4,5 2.8 Hz, H-4), 4.30 (d, 1H, J3,4 3.2 Hz, H-3),
4.18 (m, 1H, H-5), 4.15 (m, 2H, OCH2CH=CH2), 4.10 (dd,
1H, J6a,6b 8.0, J5,6a 6.0 Hz, H-6a), 3.96 (dd, J5,6b 5.0 Hz, H-6b),
2.05 (s, 3H, OAc), 1.37 (s, 3H, CH3-isop.), 1.30 (s, 3H, CH3-
isop.). 13C NMR: 135.4, 117.6 (CH=CH2), 115.7 (Cisop.), 110.6,
109.5 (HC-CCl3, C-1), 99.6 (HC-CCl3), 87.4, 85.0, 78.6 (C-2,
C-3, C-4), 75.8 (C-5), 72.3 (C-6), 26.6, 25.8, 21.3 (Me groups).
Anal. Calcd for C14H19O6Cl3: C, 43.12; H, 4.88; found: C,
43.22; H, 4.70.
obtained from trichloroethylidene acetal of D-glucose18, D-
galactose19 and D-mannose20. Monosaccharides mostly react
in their furanose forms with chloral to give trichloroethylidene
acetals.1,2-O-(R)-trichloro-ethylidene-α-D-glucofuranose is
also known α-chloralose which is commercially available
compound. It is used as an anesthetic for animals21. Further-
more, trichloroethylidine acetals are suitable protecting groups
for the synthesis of some biologically important compounds22
and antimicrobial chloralose derivatives are also known23.
Trichloroethylidine acetal derivatives (1-4) were further acetalized
with 2,2-dimethoxypropane (2,2-DMP) to give the 5,6-O-
isopropylidene derivatives (5-8)21,24,25. Then, 5,6-O-isopro-
pylidene derivatives (5-8) reacted with acetic anhyride and
catalytic amount of DMAP in pyridine/EtOAc (1/10) at room
temperature to give 3-O-acetylchloralose derivatives (5-8).
Finally, this 3-O-acetylchloralose derivatives (5-8) reacted with
allyl alcohol and Lewis acide (BF3.OEt2) in dry acetonitrile at
0 °C under argon to give 3-O-allyl ether chloralose derivatives
(9-12) (Figs. 1-3). All compounds were structurally charac-
terized by using FTIR, 1H and 13C NMR.
3-O-Allyl-5,6-O-isopropylidene-1,2-O-(R)-trichloroe-
thylidene-β-D-mannofuranose (12): The title product was
synthesized, yield 60 % (2.35 g). [α]21D -23.0 (c 1, CH2Cl2).
(KBr, νmax, cm-1): 2983-2897 (C-H), 1619 (C=C), 1153 (COC),
798 (CH-Cl). 1H NMR (CDCl3, 400 MHz): δ 5.94 (d, 1H, J1,2
4.0 Hz, H-1), 5.82 (m, 1H, CH2CH=CH2), 5.74 (s, 1H, HCCl3),
5.30 (dd, 1H, CH2CH=CH2, J = 17.3, 1.3 Hz), 5.16 (dd, 1H,
CH2CH=CH2, J = 10.2, 1.4 Hz), 5.10 (d, 1H, H-2), 4.52 (dd,
1H, J4,5 2.8 Hz, H-4), 4.43 (m, 1H, H-5), 4.28 (d, 1H, J3,4 3.2
Hz, H-3), 4.19 (m, 2H, OCH2CH=CH2), 4.12 (dd, 1H, J6a,6b
8.6, J5,6a 6.3 Hz, H-6a), 3.94 (dd, J5,6b 5.6 Hz, H-6b), 2.09 (s,
3H, OAc), 1.41 (s, 3H, CH3-isop.), 1.37 (s, 3H, CH3-isop.).
13C NMR: 134.9, 116.5 (CH=CH2), 117.9 (Cisop.), 107.6, 102.5
(HC-CCl3, C-1), 99.1 (HC-CCl3), 86.4, 82.5, 76.3 (C-2, C-3,
C-4), 74.3 (C-5), 72.3 (C-6), 24.6, 21.2, 20.9 (Me groups).
Anal. Calcd for C14H19O6Cl3: C, 43.12; H, 4.88; found: C,
43.07; H, 4.79.
In the FTIR spectrum of the acetyl derivatives (5-8), the
characteristic absorptions for C=O (carbonyl), COC (ether)
and CH-Cl (acetal) groups were observed approximately at
1710, 1150 and 797 cm-1, repectively. In the 1H NMR spectrum
of the 3-O-acetyl-5,6-O-isopropylidene of chloralose deriva-
tives (5-8), the methyl protons (3H, OAc) appeared as a siglet
1
approximetly at 2 ppm, unlike the H NMR spectrum of the
5,6-O-isopropylidene of chloralose derivatives (1-4). Also, in
the 13C NMR spectrum of the 3-O-acetyl-5,6-O-isopropylidene
of chloralose derivatives (5-8) were observed the peak of the
carbonyl carbon of the acetyl group at approximately 170 ppm.
In the FTIR spectrum of the 3-O-allyl ether chloralose
derivatives (9-12), the characteristic absorptions for C=C
(allyl), COC (ether) and CH-Cl (acetal) groups were observed
approximetly 1620, 1148 and 798 cm-1, repectively. In the 1H
NMR spectrum of the 3-O-allyl-5,6-O-isopropylidene of
RESULTS AND DISCUSSION
The object of this study to prepare isopropylidene protected
allyl sacharides (9-12) in this context. These compounds were
Fig. 1. Sythesis of 3-O-allyl ether derivatives of α-chloralose (9) and β-chloralose (10)
Fig. 2. Sythesis of 3-O-allyl ether derivatives of galactochloralose (11)

356 Telli
Asian J. Chem.
Fig. 3. Sythesis of 3-O-allyl ether derivatives of mannochloralose (12)
5. G.V.M. Sharma, K. Ravinder Reddy, A.R avi Sankar and A.C. Kunwar,
Tetrahedron Lett., 42, 8893 (2001).
chloralose derivatives (9-12) appeared the specific double bond
protons at 5.80-5.10 ppm and allylic methylene protons
between 4.20 and 4.00 ppm. Furthermore, in the 13C NMR
spectrum of the 3-O-allyl-5,6-O-isopropylidene of chloralose
derivatives (9-12) were observed the peaks of the double bond
carbons at approximately 135 and 117 ppm.
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Conclusion
The new 3-O-allyl ether derivatives of sugar (9-12) were
synthesized from the 3-O-acetylchloralose derivatives (5-8)
with high yield and mild reaction conditions. All new com-
pounds were characterized by NMR and FTIR spectroscopic
methods. These new 3-O-allyl ether of chloralose derivatives
can be used as intermediates in synthetic carbohydrate chemistry
and are also potential monomers for the synthesis of new
glycopolymers.
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ACKNOWLEDGEMENTS
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The authors thank Associate Prof. Dr. Yesim Salman for
helpful discussions. Thanks are also due to Milano-Bicocca
University, Department of Bioscience and Biotechnology,
Milano, Italy for NMR, FTIR and elemental analysis.
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