Li et al.
ture. After 0.5 h, 0.5 mL triethylamine was added dropwise. Then,
the mixture was refluxed for 12 h and the solvent was removed in
vacuum. The crude product was purified by silicon-gel column
eluted with ethyl acetate–petroleum ether (1:2).
ring-C), 126.95, 128.59, 129.27, 136.93 (6C, Ar-C), 158.16 (C-2),
168.23, 168.31, 169.63, 169.90, 170.03, 170.14, 170.74, 170.81 (9C,
8 · CO, C-4). Anal. Calcd. for C40H50N2O20S: C, 52.74; H, 5.53; N,
3.08; Found: C, 52.40; H, 5.83; N, 3.08. FABMS: m ⁄ z 910.89.
3-Thiazolidine acetic acid-2-[(2¢,3¢,4¢,6¢-tetra-O-acetyl-b-D-galactopyr-
anosyl)-(1 fi 4)-2¢,3¢,6¢-tri-O-acetyl-b-D-glucopyranosyl]-1¢-imino-4-oxo ethyl
ester 3k. White solid; yield (0.43 g, 52.9%); mp 96–99 ꢀC (recrystal-
3-Thiazolidine acetic acid-2-[(2¢,3¢,4¢,6¢-tetra-O-acetyl-b-D-galactopyr-
anosyl)-(1 fi 4)-2¢,3¢,6¢-tri-O-acetyl-b-D-glucopyranosyl]-1¢-imino-a-(1-
methylthio)ethyl-4-oxo ethyl ester 3o. White solid; yield (0.55 g,
1
1
lized from EtOAc–petroleum); H NMR (CDCl3): d 1.23 (t, 3H, CH3),
62%); mp 97–99 ꢀC (recrystallized from EtOAc–petroleum ether); H
1.93.1.97, 1.99, 2.02, 2.09, 2.10, 2.13 (7s, 21H, 7 · OAc), 3.73–5.38
(m, 20H, OCH2, CH2,CH2COO, sugar ring-H); 13C NMR (CDCl3): d 14.24
(CH3), 20.68, 20.81, 20.98, 21.09 (7C, 7 · OAc), 33.17 (C-5), 44.08
(NCH), 62.30, 66.86, 69.32, 69.65, 70.85, 70.93, 71.19, 71.33, 72.69,
73.26, 75.00, 83.34, 101.21 (13C, sugar ring-C, CH2O), 158.05 (C-2),
166.88, 169.25, 169.61, 169.74, 169.97, 170.32, 170.54, 170.85,
171.02 (9C, 9 · CO). Anal. Calcd. for C33H44N2O20S: C, 48.29; H, 5.40;
N, 3.41; Found: C, 48.09; H, 5.18; N, 3.37. FABMS: m ⁄ z 820.77.
NMR (CDCl3): d 1.16 (t, 3H, CH3), 1.92, 2.00, 2.00, 2.01, 2.03, 2.09,
2.11 (8s, 24H, 8 · OAc), 2.30 (m, 4H, SCH2CH2), 3.67–5.31 (m, 19H,
OCH2, CH2,CHCOO, sugar ring-H); 13C NMR (CDCl3): d 14.33(CH3),
15.41 (SCH3), 20.68, 20.81, 20.93, 20.98, 21.13 (7C, 7 · OAc), 26.96
(SCH2), 30.97 (CH2), 33.05 (C-5), 55.24 (NCH), 61.05, 61.77, 62.43,
66.84, 69.32, 70.91, 71.16, 72.60, 73.47, 74.90, 76.45, 87.88, 101.21
(13C, sugar ring-C, CH2O), 157.50 (C-2), 168.45, 169.28, 169.76,
170.02, 170.23, 170.32, 170.53, 171.03 (9C, 9 · CO). Anal. Calcd.
for C36H50N2O20S2: C, 48.32; H, 5.63; N, 3.13; Found: C, 48.32; H,
5.51; N, 3.12. FABMS: m ⁄ z 894.91.
3-Thiazolidine acetic acid-2-[(2¢,3¢,4¢,6¢-tetra-O-acetyl-b-D-galactopyrano-
syl)-(1 fi 4)-2¢,3¢,6¢-tri-O-acetyl-b-D-glucopyranosyl]-1¢-imino-a-methyl-4-
oxo ethyl ester 3l. White solid; yield (0.53 g, 63.4%); mp 106–108 ꢀC
(recrystallized from EtOAc–petroleum ether); 1H NMR (CDCl3): d
1.18 (t, 3H, CH3), 1.45 (d, J = 7.2 Hz, 3H, CH3), 1.94, 2.01, 2.03,
2.04, 2.11, 2.13 (7s, 21H, 7 · OAc), 3.72–5.26 (m, 18H, OCH2, CH2,
CHCOO, sugar ring-H), 5.32 (d, J = 3.2 Hz, 1H, C'-1); 13C NMR
(CDCl3): d 13.72 (CH3), 14.33 (CH3), 20.67, 20.81, 20.99, 21.13 (7C,
7 · OAc), 33.08 (C-5), 51.80 (NCH), 61.06, 61.61, 62.41, 66.84,
69.32, 70.91, 71.16, 72.62, 73.33, 74.94, 76.45, 87.96, 101.20 (13C,
sugar ring-C, CH2O), 156.85 (C-2), 169.11, 169.25, 169.73, 169.99,
170.20, 170.30, 170.51, 170.60 (9C, 9 · CO). Anal. Calcd. for
C34H46N2O20S: C, 48.92; H, 5.55; N, 3.36; Found: C, 48.44; H, 5.78;
N, 3.28. FABMS: m ⁄ z 834.80.
3-Thiazolidine acetic acid-2-[(2¢,3¢,4¢,6¢-tetra-O-acetyl-a-D-glucopyrano-
syl)-(1 fi 4)-2¢,3¢,6¢-tri-O-acetyl-b-D-glucopyranosyl]-1¢-imino-4-oxo ethyl
ester 3p. White solid; yield (0.68 g, 83.6%); mp 88–90 ꢀC (recrystal-
1
lized from EtOAc–petroleum ether); H NMR (CDCl3): d 1.27 (t, 3H,
CH3), 1.96.1.97, 1.99, 2.02, 2.03, 2.07, 2.11 (7s, 21H, 7 · OAc),
3.78–5.46 (m, 20H, OCH2, CH2,CH2COO, sugar ring-H); 13C NMR
(CDCl3): d 14.38 (CH3), 20.78, 20.88, 21.13 (7C, 7 · OAc), 33.24 (C-
5), 44.10 (NCH), 61.58, 62.15, 63.07, 68.23, 69.23, 69.58, 70.24,
72.98, 73.39, 74.37, 76.01, 83.41, 95.93 (13C, sugar ring-C, CH2O),
157.90 (C-2), 166.73, 169.60, 169.85, 170.03, 170.46, 170.70,
170.88, 171.02 (9C, 9 · CO). Anal. Calcd. for C33H44N2O20S: C,
48.29; H, 5.40; N, 3.41; Found: C, 48.22; H, 5.65; N, 3.39. FABMS:
m ⁄ z 820.77.
3-Thiazolidine acetic acid-2-[(2¢,3¢,4¢,6¢-tetra-O-acetyl-b-D-galacto-
pyranosyl)-(1 fi 4)-2¢,3¢,6¢-tri-O-acetyl-b-D-glucopyranosyl]-1¢-imino-
a-(iso-butyl)-4-oxo ethyl ester 3m. White solid; yield (0.55 g,
63.6%); mp 96–99 ꢀC (recrystallized from EtOAc–petroleum ether);
1H NMR (CDCl3): d 0.90 (d, J = 6.8 Hz, 6H, 2 · CH3), 1.19 (t, 3H,
CH3), 1.36 (m, 3H, CHCH2), 1.91, 1.94, 1.98, 2.01, 2.08, 2.10 (7s,
21H, 7 · OAc), 3.74–5.34 (m, 19H, OCH2, CH2,CHCOO, sugar ring-H);
13C NMR (CDCl3): d 14.23 (CH3), 20.70, 20.81, 20.90, 21.06, 21.81,
23.33, 25.37 (10C, 7 · OAc, Me2CH), 33.19 (C-5), 36.55 (CH2), 55.02
(NCH), 60.99, 62.07, 62.31, 66.90, 69.21, 69.74, 70.52, 70.79, 71.21,
71.81, 83.59, 87.92, 100.87 (13C, sugar ring-C, CH2O), 157.21 (C-2),
169.11, 169.17, 169.64, 170.26, 170.36, 170.49, 170.56, 170.99,
171.10 (9C, 9 · CO). Anal. Calcd. for C37H52N2O20S: C, 50.68; H, 5.98;
N, 3.19; Found: C, 50.49; H, 5.96; N, 3.32. FABMS: m ⁄ z 876.88.
3-Thiazolidine acetic acid-2-[(2¢,3¢,4¢,6¢-tetra-O-acetyl-a-D-glucopyr-
anosyl)-(1 fi 4)-2¢,3¢,6¢-tri-O-acetyl-b-D-glucopyranosyl]-1¢-imino-a-
methyl -4-oxo, ethyl ester 3q. White solid; yield (0.62 g, 74%);
1
mp 86–88 ꢀC (recrystallized from EtOAc–petroleum ether); H NMR
(CDCl3): d 1.12 (t, 3H, CH3), 1.49 (d, J = 7.2 Hz, 3H, CH3), 1.98,
2.00, 2.02, 2.04, 2.11, 2.18 (7s, 21H, 7 · OAc), 3.72–5.41 (m, 19H,
OCH2, CH2, CHCOO, sugar ring-H); 13C NMR (CDCl3): d 11.42 (CH3),
11.75(CH3), 18.21, 18.30, 18.49, 18.55 (7C, 7 · OAc), 30.57 (C-5),
49.39 (NCH), 59.58, 60.57, 65.67, 66.04, 67.01, 67.65, 69.55, 70.43,
70.48, 73.50, 80.83, 85.18, 93.09 (13C, sugar ring-C, CH2O), 154.72 (C-
2), 166.40, 166.56, 167.05, 167.35, 167.44, 167.56, 167.81, 168.01,
168.17 (9C, 9 · CO). Anal. Calcd. for C34H46N2O20S: C, 48.92; H, 5.55;
N, 3.36; Found: C, 49.10; H, 5.23; N, 3.00. FABMS: m ⁄ z 834.80.
3-Thiazolidine acetic acid-2-[(2¢,3¢,4¢,6¢-tetra-O-acetyl-b-D-galactopyr-
anosyl)-(1 fi 4)-2¢,3¢,6¢-tri-O-acetyl-b-D-glucopyranosyl]-1¢-imino-a-ben-
zyl-4-oxo ethyl ester 3n. White solid; yield (0.62 g, 68%); mp 89–
3-Thiazolidine acetic acid-2-[(2¢,3¢,4¢,6¢-tetra-O-acetyl-a-D-glucopyranosyl)-
(1 fi 4)-2¢,3¢,6¢-tri-O-acetyl-b-D-glucopyranosyl]-1¢-imino-a-(iso-butyl)-4-oxo
ethyl ester 3r. White solid; yield (0.71 g, 81%); mp 182–183 ꢀC (re-
crystallized from EtOAc–petroleum ether); 1H NMR (CDCl3): d 0.91
(d, J = 6.4 Hz, 6H, 2 · CH3), 1.22 (t, 3H, CH3), 1.38 (m, 3H, CHCH2),
1.92.1.95, 1.98, 2.02, 2.05, 2.09 (7s, 21H, 7 · OAc), 3.81–5.44 (m,
19H, OCH2, CH2, CHCOO, sugar ring-H); 13C NMR (CDCl3): d 14.30
(CH3), 20.75, 21.02, 21.08, 21.84, 23.33, 25.34 (10C, 7 · OAc,
Me2CH), 33.10 (C-5), 36.50 (CH2), 54.95 (NCH), 61.58, 62.00, 68.24,
68.57, 69.31, 69.60, 70.16, 72.05, 73.03, 73.14, 83.56, 95.63 (13C,
1
91 ꢀC (recrystallized from EtOAc–petroleum ether); H NMR (CDCl3):
d 1.22 (t, 3H, CH3), 1.99, 2.01, 2.04, 2.06, 2.09, 2.12, 2.13 (7s, 21H,
7 · OAc), 3.33–5.60 (m, 21H, OCH2, 2 · CH2, CH, sugar ring-H),
7.09–7.27 (m, 5H, Ar-H); 13C NMR (CDCl3): d 14.36 (CH3), 20.79,
20.89, 21.08, 21.15 (7C, 7 · CH3), 32.79 (C-5), 33.62 (CH2-Ar),
57.01(NHCH), 61.58, 62.21, 63.15 (3C, 3 · CH2O), 68.23, 68.75,
69.22, 70.24, 72.14, 73.15, 74.32, 76.29, 83.27, 95.88 (10C, sugar
974
Chem Biol Drug Des 2011; 78: 969–978