M. Shimamura et al. / European Journal of Medicinal Chemistry 41 (2006) 569–576
575
(2H, m), and 3.95–4.10 (1H, m) for mannose C2, C3, C4, C5,
C6a, C6b, sphingosine C1a, C1b, C2 and C3, 4.70–4.72 (1H,
m, anomeric), 7.04 (2H, d, J = 8.3 Hz, phenyl), 7.07(2H, d,
J = 8.3 Hz, phenyl). MS (EI), m/z: 677(M+).
IR (cm–1) (KBr): 3388, 2922, 2852, 2360, 1622, 1464,
1384.
2.0 Hz), and 3.94–4.03 (1H, m), for mannose C2, C3, C4,
C5, C6a, C6b, sphingosine C1a, C1b, C2 and C3, 4.72(1H,
brs, anomeric).
IR(KBr): 3306, 2917, 2850, 1644, 1543, 1468, 1139, 1105,
1059.
Mass(EI): 658.
Appearance: Colorless amorphous
CD: [α]D = +48.5 (0.20, EtOH).
m.p. 157–159.
4.2.5.2. 10b (GalC24). Elemental analysis: calculated for
C46H91NO7·3/4H2O, C, 70.50; H, 11.90; N,1.79.
Found: C, 70.57; H, 11.91; N, 1.66.
4.2.5.6. 10d (GalC2). Elemental analysis: Calculated for
C24H47NO7·1/4H2O: C, 61.84; H, 10.27; N, 3.00.
Found: C, 61.77; H, 10.38; N, 3.07.
1H-NMR (CD3OD): δ 0.80 (6H, t, 6.8 Hz, methyl), 1.19
(66H, brs, methylene), 1.45–1.60 (2H, m, methylene), 2.10
(2H, t, J = 7.3 Hz, methylene) 3.36 (1H, dd, J = 10.3,
5.4 Hz), 3.46–3.71 (6H, m), 3.77 (1H, d, J = 2.0H), and
3.90–3.94 (1H, m), for galactose C2, C3, C4, C5, C6a, C6b,
sphingosine C1a, C1b, C2 and C3, 4.70 (1H, brs, anomeric).
MS (EI): m/z: 770 (M+).
1H-NMR (400 MHz, CD3OD): δ 0.89 (3H, t, J = 8 Hz,
methyl), 1.28 (24H, brs, methylene), 1.44–1.52 (1H, m, methy-
lene), 1.53–1.61 (1H, m, methylene), 1.95 (3H, s, methyl),
3.33–3.37 (1H, m), 3.42–3.51 (1H, m), 3.63–3.79 (5H, m),
3.81 (1H, brs), and 3.90–4.03 (1H, m), for galactose C2, C3,
C4, C5, C6a, C6b, sphingosine C1a, C1b, C2 and C3, 4.79–
4.80 (1H, m, anomeric), 7.9–8.1 (1H, m, amide).
IR(KBr): 3433,2918,2850,1646,1543,1468.
m.p. 142–144 °C.
IR (cm–1) (KBr): 3278, 2915, 2851, 1648, 1558, 1472.
EI-MS, m/z: 462 (M + H)+.
4.2.5.3. 10c (ManC16). Elemental analysis: Calculated for
C38H75NO7·1/2H2O: C,68.39; H,11.45; N,2.14.
Found: C;68.42; H,11.48; N,2.10.
4.2.5.7. 10e (Man2HM4PhC16). Elemental analysis: Calcu-
lated for C41H73NO8·H2O, C,67.82; H,10.41; N,1.93.
Found: C;67.55; H,10.33; N,1.91.
1H-NMR(CD3OD): δ 0.89 (6H, t, J = 6.8 Hz, methyl), 1.28
(48H, brs, methylene), 1.59–1.67(4H, m, methylene), 2.18 (2H,
t, J = 7.3 Hz, methylene), 3.38 (1H, dd, J = 9.8, 5.9 Hz), 3.46–
3.52 (1H, m), 3.58 (1H, d, J = 9.3 Hz), 3.61–3.70 (3H, m), 3.78
(1H, dd, J = 3.4, 1.5 Hz), 3.81 (1H, dd, J = 11.7, 2.0 Hz), and
3.94–4.03 (1H, m), for mannose C2, C3, C4, C5, C6a, C6b,
sphingosine C1a, C1b, C2 and C3, 4.72 (1H, brs, anomeric)
MS (EI): m/z: 658 (M+).
1H-NMR (400 MHz, CD3OD): δ 0.89(6H, t, J = 6.8 Hz,
methyl), 1.27 (34H, brs, methylene), 1.53–1.65 (4H, m, methy-
lene), 1.93–2.08 (2H, m, methylene), 2.18–2.22 (2H, m, methy-
lene), 2.52–2.59 (4H, m, methylene), 3.52–3.57 (2H, m), 3.61–
3.73 (4H, m), and 3.79–3.84 (4H, m), for mannose C2, C3, C4,
C5, C6a, C6b, sphingosine C1a, C1b, C2 and C3, 4.75 (1H, d,
J = 9.8 Hz, anomeric), 7.04 (2H, d, J = 7.8 Hz, phenyl), 7.08
(2H, d, J = 7.8 Hz, phenyl), 7.30 (1H, d, J = 11.2 Hz, amide).
IR (KBr): 3321, 2923, 2853, 1646, 1467.
m.p. 153–155 °C.
4.2.5.4. 2S-10c. Elemental analysis: Calculated for
C38H75NO7·1/2H2O: C, 68.42; H, 11.48; N,2.10.
Found: C; 68.39; H, 11.45; N, 2.14.
Amorphas.
4.2.5.8. 10f (Gal2HM4PhC16). 1H-NMR (400 MHz, CD3OD):
δ 0.83–0.87 (6H, m, methyl), 1.22 (34H, brs, methylene), 1.50–
1.60 (4H, m, methylene), 1.90–2.08 (2H, m, methylene), 2.13–
2.20 (2H, m, methylene), 2.45–2.57 (4H, m, methylene), 3.4–
4.0 (10H, m), for galactose C2, C3, C4, C5, C6a, C6b, sphin-
gosine C1a, C1b, C2 and C3, 4.78–4.85 (1H, m, anomeric),
7.00 (2H, d, J = 8 Hz, phenyl), 7.05 (2H, d, J = 8 Hz, phenyl),
7.38 (1H, d, J = 16 Hz, amide).
1H-NMR(CD3OD): δ 89 (6H, t, J = 6.8 Hz, methyl), 1.28
(48H, brs, methylene), 1.51–1.81 (4H, m, methylene), 2.19
(2H, t, J = 7.3 Hz, methylene), 3.41 (1H, dd, J = 9.8, 4.4 Hz),
3.46–3.53 (1H, m), 3.57 (1H, d, J = 9.8 Hz), 3.58–3.71 (3H,
m), 3.78 (1H, brs), 3.82 (1H, d, J = 11.7 Hz), and 3.99–4.08
(1H, m), for mannose C2, C3, C4, C5, C6a, C6b, sphingosine
C1a, C1b, C2 and C3, 4.73 (1H, brs, anomeric).
IR (KBr): 3296, 2918, 2851, 1643, 1541, 1467, 1130, 1101,
1059.
High resolution FAB-MS, calculated for C41H74 N1O8 (M +
H)+ 708.5414; found 708.5435.
CD: [α]D: +19.2 (0.25, EtOH).
m.p. 147–148.
1
4.2.5.9. 10g (Gal2HM4PhC8). H-NMR (400 MHz, CD3OD):
δ 0.84–0.92 (6H, m, methyl), 1.28 (18H, brs, methylene), 1.50–
1.65 (4H, m, methylene), 1.90–2.10 (2H, m, methylene), 2.13–
2.25 (2H, m, methylene), 2.45–2.60 (4H, m, methylene), 3.4–
4.1 (10H, m), for galactose C2, C3, C4, C5, C6a, C6b, sphin-
gosine C1a, C1b, C2 and C3, 4.78–4.85 (1H, m, anomeric),
7.04 (2H, d, J = 8 Hz, phenyl), 7.09 (2H, d, J = 8 Hz, phenyl),
7.42 (1H, d, J = 12 Hz, amide).
4.2.5.5. 2R-10c.
C38H75NO7·1/2H2O: C, 68.42; H,11.48; N, 2.10.
Found: C; 68.39; H, 11.45; N, 2.14
NMR(CD3OD): δ 0.89(6H, t, J = 6.8 Hz, methyl), 1.28
(48H, brs, methylene), 1.59–1.67 (4H, m, methylene), 2.18
(2H, t, J = 7.3 Hz, methylene), 3.38 (1H, dd, J = 9.8, 5.9 Hz),
3.46–3.52 (1H, m), 3.58 (1H, d, J = 9.3 Hz), 3.61–3.70 (3H,
m), 3.78 (1H, dd, J = 3.4, 1.5 Hz), 3.81 (1H, dd, J = 11.7,
Elemental
analysis:
Calculated
for
High resolution FAB-MS, calculated for C33H58 N1O8 (M +
H)+, 596.4162; found 596.4153.