F. Iglesias-Guerra et al. / Carbohydrate Research 316 (1999) 71–84
79
NMR (200 MHz, Me2SO-d6): l 7.72 (d, 1 H,
J2,NH 8.4 Hz, N–H), 7.5–7.3 (m, 5 H, Ph),
7.01, 6.64 (2 d, 4 H, J 8.6 Hz, p-C6H4), 5.58 (s,
1 H, PhCH), 5.22 (d, 1 H, J3,OH 5.3 Hz, OH),
4.46 (d, 1 H, J1,2 7.9 Hz, H-1), 4.18 (dd, 1 H,
J5,6e 4.7, J6e,6a 10.4 Hz, H-6e), 2.40 (t, 2 H, J
7.3 Hz, CH2Ar), 2.06 (t, 2 H, J 7.3 Hz,
CH2CON), 1.75 (m, 2 H, Ar–CH2 –CH2–
CH2–CON), 1.5–1.1 [(CH2)6], 0.83 (t, 3 H, J
6.8 Hz, CH3); 13C NMR (50 MHz, Me2SO-d6):
l 171.8 (CꢀO), 144.3, 137.8, 130.0, 129.2,
128.8, 128.0, 126.3, 111.8 (2Ar), 101.6
(PhCH), 100.6 (C-1), 81.4 (C-4), 70.4 (C-3),
68.7 (OCH2R), 67.9 (C-6), 66.0 (C-5), 56.0
(C-2), 52.2 (NCH2), 41.1 (CH2Cl), 35.3, 33.5,
31.2, 29.1, 28.8, 28.7, 27.4, 25.4, 22.2 [9(CH2)],
13.9 (CH3). Anal. Calcd for C35H50Cl2N2O6:
C, 63.15; H, 7.57; N, 4.21. Found: C, 63.11;
H, 7.62; N, 4.19.
temperature for 12 h. Then, a new portion of
reactive soln (1.5 mmol) was added and the
mixture was stirred for a further 12 h. The
reaction was diluted with CH2Cl2, washed suc-
cessively with aq 5% soln of NaOH and water,
then dried (Na2SO4) and concentrated to dry-
ness. The solid obtained was purified by flash
chromatography on silica gel using CH2Cl2–
MeOH mixtures as eluents.
1-Hexyl glucopyranoside deri6ati6e 17. 1.0 g
(72%); mp 195–197 °C; [h]D −6.9° (c 0.3,
1
DMF); FABMS: m/z 659 (100%) [MNa+]; H
NMR (200 MHz, Me2SO-d6): l 7.73 (d, 1 H,
J2,NH 8.2 Hz, N–H), 7.5–7.3 (m, 5 H, Ph),
7.03, 6.62 (2 d, 4 H, J 8.6 Hz, p-C6H4), 5.58 (s,
1 H, PhCH), 5.23 (d, 1 H, J3,OH 5.3 Hz, OH),
4.45 (d, 1 H, J1,2 7.9 Hz, H-1), 4.18 (dd, 1 H,
J5,6e 4.7, J6e,6a 10.2 Hz, H-6e), 2.40 (t, 2 H, J
7.3 Hz, CH2Ar), 2.15 (t, 2 H, J 7.3 Hz,
CH2CON), 1.8–1.1 [5(CH2)], 0.83 (t, 3H, J 6.7
Hz, CH3); 13C NMR (50 MHz, Me2SO-d6): l
171.8 (CꢀO), 144.3, 137.7, 129.3, 128.8, 128.0,
126.3, 111.8 (2Ar), 101.6 (PhCH), 100.6 (C-1),
81.3 (C-4), 70.4 (C-3), 68.7 (OCH2R), 67.9
(C-6), 66.0 (C-5), 56.0 (C-2), 52.2 (NCH2),
41.1 (CH2Cl), 35.3, 33.5, 31.0, 29.1, 27.5, 25.0,
22.0 [7(CH2)], 13.9 (CH3). Anal. Calcd for
C33H46Cl2N2O6: C, 62.16; H, 7.27; N, 4.39.
Found: C, 62.07; H, 7.49; N, 4.51.
Cyclohexyl glucopyranoside deri6ati6e 18.
1.0 g (76%); mp 163–165 °C; [h]D −37.2° (c
0.6, DMF); FABMS: m/z 657 (85%) [MNa+];
1H NMR (200 MHz, Me2SO-d6): l 7.71 (d, 1
H, J2,NH 8.4 Hz, N–H), 7.5–7.3 (m, 5 H, Ph),
7.00, 6.64 (2 d, 4 H, J 8.6 Hz, p-C6H4), 5.57 (s,
1 H, PhCH), 5.21 (d, 1 H, J3,OH 5.3 Hz, OH),
4.59 (d, 1 H, J1,2 7.8 Hz, H-1), 4.18 (dd, 1 H,
J5,6e 4.5, J6e,6a 10.0 Hz, H-6e), 2.08 (t, 2 H, J
7.2 Hz, CH2CON), 1.8–1.0 [6(CH2)]; 13C
NMR (50 MHz, Me2SO-d6): l 171.8 (CꢀO),
144.3, 137.8, 130.0, 129.3, 128.8, 128.0, 126.3,
111.9 (2Ar), 100.6 (PhCH), 99.9 (C-1), 81.4
(C-4), 75.8 (OCH), 70.3 (C-3), 68.0 (C-6), 65.9
(C-5), 56.5 (C-2), 52.2 (NCH2), 41.1 (CH2Cl),
35.3, 33.5, 32.9, 31.1, 27.3, 25.2, 23.2, 22.9
[8(CH2)]. Anal. Calcd for C33H44Cl2N2O6: C,
62.37; H, 6.63; N, 4.30. Found: C, 62.36; H,
6.98; N, 4.41.
1-Dodecyl glucopyranoside deri6ati6e 20. 1.2
g (79%); mp 150–152 °C; [h]D −67.0° (c 1.1,
1
DMF); FABMS: m/z 743 (18%) [MNa+]; H
NMR (200 MHz, CDCl3): l 7.6–7.3 (m, 5 H,
Ph), 7.10, 6.60 (2 d, 4 H, J 8.6 Hz, p-C6H4),
5.67 (d, 1 H, J2,NH 8.9 Hz, N–H), 5.55 (s, 1 H,
PhCH), 4.70 (d, 1 H, J1,2 8.2 Hz, H-1), 4.30
(dd, 1 H, J5,6e 4.6, J6e,6a 9.9 Hz, H-6e), 4.12 (t,
1 H, J5,6a =J6e,6a 9.9 Hz, H-6a), 2.55 (t, 2 H, J
7.3 Hz, CH2Ar), 2.20 (t, 2 H, J 7.2 Hz,
CH2CON), 1.91 (m, 2 H, Ar–CH2 –CH2–
CH2–CON), 1.7–1.1 [(CH2)10], 0.85 (t, 3 H, J
13
6.4 Hz, CH3); C NMR (50 MHz, CDCl3): l
172.2 (CꢀO), 144.3, 137.0, 130.7, 129.7, 129.3,
128.3, 126.1, 112.1 (2Ar), 101.9 (PhCH), 100.5
(C-1), 81.7 (C-4), 71.2 (C-3), 70.1 (OCH2R),
68.6 (C-6), 66.2 (C-5), 59.3 (C-2), 53.2
(NCH2), 40.4 (CH2Cl), 36.0, 33.9, 31.9, 29.7,
29.6, 29.4, 29.3, 27.4, 25.9, 22.7 [13(CH2)],
14.1 (CH3). Anal. Calcd for C39H58Cl2N2O6:
C, 64.90; H, 8.10; N, 3.88. Found: C, 65.15;
H, 8.01; N, 3.50.
1-Dodecyl allopyranoside deri6ati6e 21. 1.2 g
(79%); mp 156–158 °C; [h]D −51.8° (c 0.8,
1
DMF); FABMS: m/z 743 (42%) [MNa+]; H
NMR (200 MHz, CDCl3): l 7.5–7.3 (m, 5 H,
Ph), 7.06, 6.60 (2 d, 4 H, J 8.6 Hz, p-C6H4),
5.85 (d, 1 H, J2,NH 8.9 Hz, N–H), 5.57 (s, 1 H,
PhCH), 4.63 (d, 1 H, J1,2 8.2 Hz, H-1), 4.36
(dd, 1 H, J5,6e 4.6, J6e,6a 9.9 Hz, H-6e), 4.2 (m,
2 H, H-2, H-3), 2.55 (t, 2 H, J 7.3 Hz,
CH2Ar), 2.20 (t, 2 H, J 7.2 Hz, CH2CON),
1-Octyl glucopyranoside deri6ati6e 19. 1.2 g
(88%); mp 193–195 °C; [h]D −50.8° (c 0.3,
1
DMF); FABMS: m/z 687 (100%) [MNa+]; H