DESIGN, SYNTHESIS, AND PROPERTIES OF NEOGLYCOLIPIDS
1053
(
79), 452.3 (40), 468.3 (35).
ω-(Octadecylcarbamoyl)poly(oxydimethylene)car-
boxylic acid (XIII). Yield 0.35 g (66%), colorless amor-
1
.50–1.65 m (4H, CH CH OCO), 1.82–1.90 m (2H,
2
2
β-CH ), 2.29–2.37 m (2H, δ-CH ), 3.58 s [~290H,
2
2
(CH CH O) ], 3.97 t (2H, CH OCO, J 6.8 Hz), 4.06 t (2H,
2 2 n 2
–
1
phous substance, R 0.50 (I). IR spectrum, ν, cm : 3437
(
(
9
f
CH OCO, J 6.8 Hz), 4.07 s (2H, CH CONH), 4.08 s (2H,
2 2
CH COOH), 4.54–4.61 m (1H, α-CH). Mass spectrum,
m/z (I , %): 3957.3 [M] (CpedHee зHaчeHande), 3980.3
(48), 3996.2 (39).
OH), 2890 (CH), 1726 (C=O acid), 1621 (C=O), 1577
2
NH), 1469 (CH), 1359 (CH), 1278 (C–O), 1115 (C–O),
+
rel
1
45 (C–O), 847. H NMR spectrum, δ, ppm: 0.78 t (3H,
CH , J 6.5 Hz), 1.15 s (30H, CH ), 1.54–1.65 m (2H,
3
2
4-{[4-O-(β-D-Galactopyranosyl)-β-D-glucopyrano-
syloxy]carbamoyl}-3-oxa-N-octadecyl-butanamide.
Glycolipid (XVII). To a solution of 0.200 g (0.52 mmol)
of acid XI in 10 ml DMF was added 0.16 g (0.78 mmol) of
N,N'-dicyclohexylcarbodiimide and 0.016 g (0.13 mmol)
of 4-dimethylaminopyridine. The mixture was stirred for
CH CH NH), 3.13–3.20 m (2H, CH NH), 3.54 s [290H,
2
2
2
(
CH CH O) ], 3.88 s (2H, CH CONH), 4.04 s (2H,
2 2 n 2
+
CH COOH). Mass spectrum, m/z (I , %): 3687.2 [M]
2
rel
(
mean value), 3710.4 (35), 3726.4 (40).
-Oxa-4-[1,3-di(tetradecylcarbonyloxy)propyl-
carbamoyl]butanoic acid (XIV). Yield 0.60 g (65%),
3
1
5 min at 0°C, then 0.19 g (0.52 mmol) of compound
III was added, and the reaction mixture was stirred for
4 h at room temperature in a nitrogen atmosphere. On
–1
colorless crystals, R 0.30 (B). IR spectrum, ν, cm : 3141
f
2
(OH), 2915 (CH), 1733 (C=O), 1703 (C=O acid), 1649
completion of the reaction the separated precipitate was
filtered off, the solvent was distilled off in a vacuum,
the reaction product was chromatographed on a column
using system D as eluent. Yield 0.19 g (51%), colorless
(
1
C=O), 1559 (NH), 1462 (CH), 1401 (CH), 1240 (C–O),
122 (C–O), 854. H NMR spectrum, δ, ppm: 0.82 t (6H,
1
CH , J 6.7 Hz), 1.19 s (44H, CH ), 1.43–1.70 m (4H,
3
2
CH CH OCO), 1.92–2.05 m (1H, β-CH ), 2.10–2.21 m
2
2
2
–1
crystals, R 0.50 (E). IR spectrum, ν, cm : 3345 (OH),
f
(
1H, β-CH2), 2.28–2.44 m (2H, δ-CH ), 3.99 t (2H, CH O-
2 2
3334 (NH), 1721 (C=O), 1634 (C=O), 1556 (NH), 2934,
2880, 1384, 709 (CH), 1144–1027 (4 bands, carbohydrate
CO, J 6.8 Hz), 4.06 t (2H, CH OCO, J 6.9 Hz), 4.07 s
2
(
2H, CH CONH), 4.10 s (2H, CH COOH), 4.54–4.61 m
+
2
2
skeleton). Mass spectrum, m/z (I , %): 724.3 [M] (73),
rel
+
(1H, α-CH). Mass spectrum, m/z (I , %): 655.4 [M] (80),
747.4 (52), 763.4 (50).
rel
6
78.4 (30), 694.4 (55).
,6-Dioxa-7-[1,3-di(tetradecylcarbonyloxy)propyl-
carbamoyl]heptanoic acid (XV). Yield 0.46 g (66%),
Compounds XVIII–XXII were prepared similarly.
3
7-{[4-O-(β-D-Galactopyranosyl)-β-D-glucopyrano-
syloxy]carbamoyl}-3,6-dioxa-N-octa-decylheptan-
amide. Glycolipid (XVIII). Yield 0.12 g (54%), colorless
–
1
colorless crystals, R 0.55 (F). IR spectrum, ν, cm :
3
f
–
1
337 (OH), 2917 (CH), 2847 (CH), 1734 (C=O), 1724
crystals, R 0.30 (E). IR spectrum, ν, cm : 3250 (OH),
f
(
(
C=O acid), 1664 (C=O), 1531 (NH), 1464 (CH), 1394
CH), 1264 (C–O), 1121 (C–O), 720. 1H NMR spec-
2916 (CH), 2850 (CH), 1668 (C=O), 1542 (NH), 1463
(CH), 1399 (CH), 1207 (C–O), 1163–1020 (C–O, 4
bands, carbohydrate skeleton), 1122 (C–O), 716 (CH).
trum, δ, ppm: 0.81 t (6H, CH , J 6.9 Hz), 1.18 s (44H,
CH ), 1.47–1.59 m (4H, CH CH OCO), 1.80–1.92 m
(
CH CH O) 3.99 t (2H, CH OCO, J 6.9 Hz), 4.06 t (2H,
CH OCO, J 6.8 Hz), 4.08 s (2H, CH CONH), 4.09 s (2H,
CH COOH), 4.53–4.60 m (1H, α-CH). Mass spectrum,
m/z (I , %): 699.5 [M] (86), 722.4 (39), 738.4 (35).
3
+
Mass spectrum, m/z (I , %): 768.3 [M] (68), 791.4
rel
2
2
2
(44), 807.4 (63).
2H, β-CH ), 2.31–2.38 m (2H, δ-CH ), 3.70 s (4H,
2 2
ω-{[4-O-(β-D-Galactopyranosyl)-β-D-gluco-
pyranosyloxy]carbamoyl}poly(oxydimethylene)-N-
octadecylcarboxamide. Glycolipid (XIX). Yield 0.14
2
2
2
2
2
2
g (48%), colorless crystals. R 0.35 (F). IR spectrum, ν,
+
f
rel
–
1
cm : 3369 (OH), 2917 (CH), 2853 (CH), 1710 (C=O),
654 (C=O), 1539 (NH), 1456 (CH), 1347 (CH), 1246
C–O), 1099 (C–O), 1100–1029 (C–O, carbohydrate
skeleton), 946 (C–O), 836 (CH). Mass spectrum, m/z (I ,
ω-[1,3-Di(tetradecylcarboxy)propylcarbamoyl]
poly(oxydimethylene)carboxylic acid (XVI). Yield
0
(
(
(
1
(
.47 g (61%), colorless amorphous substance, R 0.50
f
rel
–
1
I). IR spectrum, ν, cm : 3470 (OH), 3331 (NH), 2910
+
%
): 4026.3 [M] (mean value).
CH), 2877 (CH), 1743 (C=O), 1702 (C=O acid), 1625
1
-(4-{[4-O-(β-D-Galactopyranosyl)-β-D-gluco-
C=O), 1543 (NH), 1466 (CH), 1357 (CH), 1284 (C–O),
pyranosyloxy]carbamoyl}-3-oxabutyryl-amino)
propane-1,3-diyl bispentadecanoate. Glycolipid (XX).
1
1
113 (C–O), 954 (C–O), 846 (CH). H NMR spectrum
,
δ, ppm: 0.81 t (6H, CH , J 6.6 Hz), 1.19 s (44H, CH2),
3
Yield 0.20 g (54%), colorless crystals, R 0.50 (D). IR
f
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 48 No. 8 2012