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MHz, CDCl3) d (ppm): 7.65 (d, 1H, J = 9.2 Hz, NH), 6.54, (br s,
1H, NH), 6.23 (br s, 1H, NH), 5.55 (d, 1H, J = 9.2 Hz, H-1), 5.38–
5.35 (m, 1H, H-2), 5.24 (t, 1H, H-4), 5.15 (dd, 1H, J = 3.2, 10.4
Hz, H-3), 4.40 (dd, 1H, –COCH2NH–), 4.28 (dd, J = 5.2 & 12.4
Hz, H-6a), 4.20 (dd, 1H, –COCH2NH–), 4.07 (dd, J = 2.0 & 12.4
Hz, H-6b), 3.84–3.77 (m, 1H, H-5), 3.34 (br s, 2H, –CONHCH2–),
2.25, 2.10, 2.05, 1.98 (4s, 12H, 4 6 –OCOCH3), 1.63–1.54 (m,
2H), 1.40–1.22 (m, 10 H), 0.88 (t, 3H, J = 7.2 Hz, –CH3); 13C-NMR
(100 MHz, CDCl3) d (ppm): 182.4 (CS), 171.3, 171.0, 170.8, 170.6,
170.0 (5 6 CO), 76.1 (C-1), 73.8, 71.7, 69.4, 65.3, 62.3 (C-6), 48.1,
45.1, 31.8, 29.3, 29.2, 29.1, 27.0, 22.7, 21.2, 20.9, 20.8, 14.2
(–CH3); ESI-MS (m/z): calcd for C25H42N3O10S: 576.2591 ([M +
H]+), found: 576.2595.
1-N-(2-Deoxy-2-acetamido-3,4,6-tri-O-acetyl-b-D-glucopyrano-
syl)-N99-(n-dodecyl)thioureidoacetamide (25). White solid;
m.p.: 134–136 uC; [a]D30: 24u (c = 1.0, CHCl3); IR (KBr , cm21):
3444, 3394, 3322, 3067, 2927, 2856, 1748, 1664, 1547, 1436,
1375, 1242, 1114, 1046, 963, 907, 680, 669, 665, 647, 680, 669,
665, 647, 602, 558, 546, 509; 1H-NMR (400 MHz, CDCl3) d
(ppm): 7.73 (d, 1H, J = 8.0 Hz, NH), 6.75, (br s, 3H, NH), 5.28
(br s, 1H, H-1), 5.25 (t, 1H, J = 9.6 Hz, H-3), 5.10 (t, 1H, H-4),
4.50–4.05 (m, 5 H, H-2, H-6a, H-6b & –COCH2NH–), 3.91–3.80
(m, H-5), 3.43 (br s, 2H, –CONHCH2–), 2.09, 2.07, 2.04, 1.97 (4s,
12H, 3 6 –OCOCH3 & –NHCOCH3), 1.65–1.54 (m, 2H), 1.44–
1.22 (m, 10 H), 0.88 (t, 3H, –CH3); 13C-NMR (100 MHz, CDCl3) d
(ppm): 183.3 (CS), 172.3, 171.6, 171.1, 170.8, 169.4 (5 6 CO),
79.8 (C-1), 73.7, 73.4, 68.7, 62.2 (C-6), 53.4, 48.1, 44.8, 31.9,
29.4, 29.3, 29.2, 27.1, 23.3, 22.7, 20.8, 20.6, 14.1 (–CH3); ESI-MS
(m/z): calcd for C25H43N4O9S: 575.2751 ([M + H]+), found:
575.2752.
1-N-(2,3,4-Tri-O-acetyl-a-L-rhamnopyranosyl)-N99-(n-octyl)-
thioureidoacetamide (26). White solid; m.p.: 41–43 uC; [a]3D0:
10.9u (c = 1.0, CHCl3); IR (KBr, cm21): 3470, 3339, 3069, 2927,
2857, 1748, 1691, 1550, 1439, 1371, 1250, 127, 1167, 1088,
1054, 1025, 961, 944, 910, 875, 743, 722, 672, 655, 602, 540,
502; 1H-NMR (400 MHz, CDCl3) d (ppm): 7.72 (d, 1H, J = 9.2 Hz,
NH), 6.76, (br s, 1H, NH), 6.38 (br s, 1H, NH), 5.52 (d, 1H, J =
9.2 Hz, H-1), 5.36 (d, J = 3.2 Hz, H-2), 5.13 (d, 1H, J = 10 Hz,
H-3), 5.03 (t, 1H, J = 10 Hz, H-4), 4.45–4.17 (m, 2H, –CH2NH),
3.68 (m, 1H, H-5), 3.37 (br s, 2H, –NHCH2), 2.25, 2.06, 2.00, (3s,
9H, 3 6 –OCOCH3), 1.63–1.55 (m, 2H), 1.40–1.20 (m, 13 H),
0.88 (t, 3H, J = 6.8 Hz, –CH3); 13C-NMR (100 MHz, CDCl3) d
(ppm): 182.6 (CS), 170.7, 169.9 (3 6 CO), 75.9 (C-1), 72.1, 71.6,
70.2, 69.7, 48.1, 44.7, 31.8, 29.6, 29.2, 28.9, 26.9, 22.6, 21.1,
20.7, 17.5, 14.0 (–CH3); ESI-MS (m/z): calcd for C23H40N3O8S:
518.2536 ([M + H]+), found: 518.2531.
1-N-(2,3,4-Tri-O-acetyl-b-D-xylopyranosyl)-N99-(n-octyl)-thiour-
eidoacetamide (27). White solid; m.p.: 57–59 uC; [a]3D0: 2.5u (c =
1.0, CHCl3); IR (KBr, cm21): 3463, 3408, 3347, 3062, 2954,
2925, 2855, 1747, 1697, 1546, 1532, 1464, 1420, 1371, 1312,
1249, 1227, 1152, 1104, 1071, 1036, 984, 938, 904, 872, 767,
729, 701, 657, 604, 549, 530; 1H-NMR (400 MHz, CDCl3) d
(ppm): 7.14 (d, 1H, J = 8.8 Hz, NH), 6.54, (br s, 1H, NH), 6.34
(br s, 1H, NH), 5.32 (t, 1H, J = 9.2 Hz, H-3), 5.17 (t, 1H, J = 9.2
Hz, H-1), 5.05–4.95 (m, 1H, H-4), 4.92 (t, 1H, J = 9.2 Hz, H-2),
4.35–4.18 (m, 2H, –COCH2NH–), 4.09 (dd, J = 6.0 & 11.2 Hz,
H-5a), 3.46 (t, 1H, J = 11.2 Hz, H-5b), 3.36 (br s, 2H, –
CONHCH2–), 2.08, 2.05, 2.04, (3s, 9H, 3 6 –OCOCH3), 1.63–
1.55 (m, 2H), 1.40–1.20 (m, 10 H), 0.88 (t, 3H, J = 6.8, –CH3);
13C-NMR (100 MHz, CDCl3) d (ppm): 182.9 (CS), 1.71.4, 170.9,
169.9, 169.9 (4 6 CO), 78.6 (C-1), 72.5, 70.3, 68.9, 64.3 (C-5),
47.8, 44.7, 31.7, 29.6, 29.2, 28.9, 26.9, 22.5, 20.8, 20.6, 20.5, 14.0
(–CH3); ESI-MS (m/z): calcd for C22H37N3O8SNa: 526.2199 ([M +
Na]+). found: 576.2187.
1-N-(2,3,4-Tri-O-acetyl-a-D-arabinopyranosyl)-N99-(n-octyl)-
thioureidoacetamide (28). White solid; m.p.: 51–53 uC; [a]3D0:
252.4u (c = 1.0, CHCl3); IR (KBr, cm21): 3344, 3070, 2928, 2857,
2179, 2111, 1748, 1688, 1550, 1436, 1372, 1250, 1227, 1168,
1087, 1053, 1025, 944, 909, 875, 741, 721, 675, 656, 601, 540,
501; 1H-NMR (400 MHz, CDCl3) d (ppm): 7.08 (d, 1H, J = 8.8 Hz,
NH), 6.64, (br s, 1H, NH), 6.45 (br s, 1H, NH), 5.34 (s, 1H, H-4),
5.31–5.19 (m, 3H), 4.35–4.15 (m, 2H, –COCH2NH–), 3.99 (d,
1H, H-5a), 3.83 (d, 1H, H-5b), 3.38 (br s, 2H, –CONHCH2–),
2.16, 2.10, 2.03, (3s, 9H, 3 6 –OCOCH3), 1.64–1.54 (m, 2H),
1.42–1.22 (m, 10 H), 0.88 (t, 3H, –CH3); 13C-NMR (100 MHz,
CDCl3) d (ppm): 182.7 (CS), 171.0, 170.2, 170.1 (4 6 CO), 78.8
(C-1), 76.8, 70.6, 68.2, 68.1, 65.8 (C-5), 47.8, 45.0, 31.7, 29.2,
29.1, 28.9, 26.9, 22.5, 20.9, 20.7, 20.5, 14.0 (–CH3); ESI-MS (m/
z): calcd for C22H37N3O8SNa: 526.2199 ([M + Na]+). found:
526.2197.
1-N-(2,3,4-Tri-O-acetyl-a-L-arabinopyranosyl)-N99-(n-octyl)-
thioureidoacetamide (29). White solid; m.p.: 51–53 uC; [a]3D0:
33.4u (c = 1.1, CHCl3); IR (KBr, cm21): 3460, 3343, 3071, 2928,
2857, 1748, 1689, 1549, 1436, 1372, 1249, 1227, 1168, 1088,
1053, 1025, 944, 910, 875, 742, 721, 673, 656, 601, 502; 1H-NMR
(400 MHz, CDCl3) d (ppm): 7.03 (d, 1H, NH), 6.50 (br s, 1H,
NH), 6.33 (br s, 1H, NH), 5.34 (s, 1H, H-4), 5.29–5.11 (m, 3H),
4.37–4.18 (m, 2H, Hz, –COCH2NH–), 3.99 (dd, 1H, J = 2.0 & 13.2
Hz, H-5a), 3.83 (d, 1H, J = 13.2 Hz, H-5b), 3.36 (br s, 2H,
–CONHCH2–), 2.16, 2.10, 2.03, (3s, 9H, 3 6 –OCOCH3), 1.64–
1.54 (m, 2H), 1.42–1.22 (m, 10 H), 0.88 (t, 3H, J = 6.4 Hz, –CH3);
13C-NMR (100 MHz, CDCl3) d (ppm): 182.5 (CS), 171.3, 170.3,
170.2, 170.0 (4 6 CO), 78.9 (C-1), 70.7, 68.3, 68.1, 65.9 (C-5),
47.9, 45.1, 31.8, 29.3, 29.2, 28.9, 27.0, 22.6, 21.0, 21.0, 20.7, 14.1
(–CH3); ESI-MS (m/z): calcd for C22H37N3O8SNa: 526.2199 ([M +
Na]+), found: 576.2198.
1-N-[4-O-(29,39,49,69-Tetra-O-acetyl-b-D-galactopyranosyl)-
2,3,6-tri-O-acetyl-b-D-glucopyranosyl]-N99-(n-octyl)-thioureidoa-
cetamide (30). White solid; m.p.: 146–148 uC; [a]3D0: 21.7u (c =
1.0, CHCl3); IR (KBr, cm21): 3465, 3366, 3068, 2928, 2857,
1752, 1548, 1436, 1372, 1231, 1172, 1132, 1051, 985, 954, 906,
717, 646, 603, 548, 505; 1H-NMR (400 MHz, CDCl3) d (ppm):
6.99 (br s, 1H, NH), 6.43 (br s, 1H, NH), 6.25 (br s, 1H, NH),
5.36 (d, 1H, J = 2.8 Hz, H-4), 5.30 (t, 1H, J = 9.2 Hz, H-3), 5.20 (t,
1H, J = 9.2 Hz, H-1), 5.10 (m, 1H, H-29), 4.96 (dd, 1H, H-39), 4.86
(t, 1H, H-2), 4.55–4.40 (m, 2H, H-19 & H-6a), 4.39–4.04 (m, 5H,
–COCH2NH–, H-5, H-6b & H-69a), 3.94–3.70 (m, 3H, H-4, H-5 &
H-69b), 3.34 (br s, 2H, –CONHCH2–), 2.16, 2.13, 2.07, 2.06, 2.05,
2.04, 1.97 (7s, 21H, 7 6 OCOCH3), 1.67–1.55 (m, 2H), 1.43–
1.22 (m, 10 H), 0.88 (t, 3H, –CH3); 13C-NMR (100 MHz, CDCl3) d
(ppm): 182.4 (CS), 170.8, 170.4, 170.3, 170.1, 170.0, 169.5, 169.1
(8 6 CO), 100.7 (C-19), 77.7 (C-1), 75.7, 74.4, 72.8, 70.9, 70.5,
69.0, 66.7, 61.9 60.7, 47.7, 44.6, 31.6, 29.5, 29.1, 29.1, 26.8, 22.5,
20.8, 20.7, 20.6, 20.5, 20.4, 13.9 (–CH3); ESI-MS (m/z): calcd for
C
37H57N3O18SNa: 886.3256 ([M + Na]+), found: 886.3254.
14536 | RSC Adv., 2013, 3, 14528–14542
This journal is ß The Royal Society of Chemistry 2013