Synthesis and biological activity of α-galactosyl ceramide KRN7000 and galactosyl (α1→2) galactosyl ceramide

2 = 8.6 Hz, H-1b^Cer), 1.86 (m, 2H, H-5a^Cer, H-5b^Cer), 1.24 (m, 24H, CH2), 0.96, 1.12 (2s, 18H,
2 × t-Bu), 0.88 (3H, t, CH3); ¹³C NMR (75 MHz, CDCl3): δ 98.5 (C-1); HRMS calcd for
C₆₀H₇₉N₃O₁₂Si [M+Na]⁺: 1084.5433, found 1084.5402. Compound 10: ¹H NMR (CDCl₃): δ 7.97-
8.07 (4H, m, Ar-H), 7.54-7.67 (2H, m, Ar-H), 7.39-7.52 (4H, m, Ar-H), 5.63 (1H, dd, J₃,₄ = 4.8,
J_3,2 = 6.8 Hz, H-3^Cer), 5.55 (1H, ddd, J_4,5a = 4.2, J_4,5b = 8.5 Hz, H-4^Cer), 5.43 (d, 1H, J_4,3 =^, 2.6 Hz,
H-4), 5.13 (dd, 1H, J3,2 = 10.6 Hz, H-3), 4.85 (d, 1H, J1,2 = 3.8 Hz, H-1), 4.17-4.26 (2H, m, H-6a,
H-6b), 4.07 (m, 2H, H-5, H-2^Cer), 4.00 (m, 1H, H-1a^Cer), 3.94 (1H, dd, H-2), 3.71 (dd, 1H, J1a,
1b = 10.4, J1b,2 = 6.5 Hz, H-1b^Cer), 2.40 (d, 1H, J2,OH = 2.8 Hz, OH), 2.13, 2.04, 2.00 (3s, 9H,
3 × OCOCH3), 1.88 (m, 2H, H-5a^Cer, H-5b^Cer), 1.21 (m, 24H, CH2), 0.88 (3H, t, CH3); ¹³C NMR
(75 MHz, CDCl₃): δ 97.8 (C-1); HRMS calcd for C₄₄H₆₁N₃O₁₃ [M+Na]⁺: 862.4204, found
862.4199. Compound 11: ¹H NMR (CDCl₃): δ 7.90-8.03 (8H, m, Ar-H), 7.30-7.59 (12H, m, Ar-
H), 5.58-5.60 (2H, m, H-2', H-3'), 5.41-5.46 (3H, m, H4‘, H4, H-4C^er), 5.32-5.36 (m, 1H, H-3Ce^r),
5.32 (dd, 1H, J3,2 = 10.1, J3,4 = 3.5 Hz, H-3), 4.86 (d, 1H, J1,2 = 3.6 Hz, H-1), 4.76 (1H, br s, H-1’),
4.09-4.20 (3H, m, H-2, H-6a, H-6b), 3.88-4.06 (m, 6H, H-5, H-5', H-6a', H-6b', H-1aC^er, H-2 Cer),
3.52 (dd, 1H, J1a,1b = 9.9, J1b,2 = 8.5 Hz, H-1b^Cer), 2.12, 2.09, 2.01 (3s, 9H, 3 × OCOCH3), 1.83
(m, 2H, H-5a^Cer, H-5b^Cer), 1.29 (m, 24H, CH₂), 0.95, 1.09 (2s, 18H, 2 × t-Bu), 0.86 (3H, t, CH₃);
¹³C NMR (75 MHz, CDCl₃): δ 98.9 (C-1^,), 97.9 (C-1); HRMS calcd for C₇₂H₉₅N₃O₂₀Si [M+Na]
⁺: 1372.6278, found 1372.6251. 1: HRMS calcd for C49H97NO9 [M+Na]⁺: 880.7239, found
880.7218. Compound 12: HRMS calcd for C56H109NO14 [M+Na]⁺:1042.7848, found 1042.7837.

Published as: Bioorg Med Chem Lett. 2009 August 01; 19(15): 4288-4291.

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