ganglioside GD1α | 143571-76-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 鞘脂
• 英文名称: ganglioside GD1α
• 英文别名: (2R,4S,5R,6R)-5-acetamido-2-[[(2R,3R,4R,5R,6S)-5-acetamido-4-[(2R,3R,4S,5S,6R)-4-[(2S,4S,5R,6R)-5-acetamido-2-carboxy-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxan-2-yl]oxy-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-6-[(2R,3R,4R,5R,6S)-6-[(2R,3S,4R,5R,6R)-4,5-dihydroxy-2-(hydroxymethyl)-6-[(E,2S,3R)-3-hydroxy-2-(octadecanoylamino)octadec-4-enoxy]oxan-3-yl]oxy-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy-3-hydroxyoxan-2-yl]methoxy]-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
• CAS: 143571-76-0
• 化学式: C₈₄H₁₄₈N₄O₃₉
• 分子量: 1838.1
• InChiKey: VZTIKCUHBVDWLM-KXZFRSNYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  127
• 可旋转键数：
  59
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  686
• 氢给体数：
  25
• 氢受体数：
  39

反应信息

• 作为产物：
  描述：

  C₈₆H₁₅₂N₄O₃₉ 在 Amberlite IR-120 (H⁺) 作用下， 以 甲醇 、 水 为溶剂， 反应 16.0h， 以52.5 mg的产率得到ganglioside GD1α
  参考文献：
  名称：

  双唾液酸神经节苷脂GD1α及其位置异构体的合成

  摘要：

  摘要描述了双唾液酸神经节苷脂GD1α及其α2-6位置异构体的第一个全合成。衍生自已知五糖前体的适当保护的五糖衍生物被选作糖基受体。使用我们简便的唾液酸立体选择性α-糖基化方法，将这些受体与甲基（甲基5-乙酰氨基-4,7,8,9-四-O-乙酰基-3,5-二脱氧-2-硫代-d偶联-在二甲基（甲硫基）ulf三氟甲磺酸盐（DMTST）存在下，在乙腈介质中的甘油-d-半乳糖-2-壬基吡喃糖苷）酸酯，以中等收率得到所需的二α-唾液酸六assa糖衍生物。与（2 S，3 R，4 E）-2-叠氮基-3-O-苯甲酰基-4-十八碳烯-1，3-二醇偶联时，六氯化亚氨基三乙酰氨基磺酸酯高产率地得到相应的β-连接的鞘氨醇糖苷。

  DOI：

  10.1016/s0008-6215(00)90922-4

文献信息

• A HIGHLY EFFICIENT TOTAL SYNTHETIC ROUTE TO α-SERIES GANGLIOSIDES: GM1α, GD1α, AND GT1α1-2
  作者：Hiromi Ito、Hideharu Ishida、Makoto Kiso

  DOI：10.1081/car-100103959

  日期：2001.3.31

  A highly efficient total synthetic route to alpha -series gangliosides GM1 alpha, GD1 alpha and GT1 alpha is described. The suitably protected gangliotriose (GgOse3) derivatives, i.e., 2-(trimethylsilyl)ethyl (2-acetamido-2-deoxy-3-O-p-methoxybenzyl-beta -D-galactopyranosyl)-(1-->4)-(2,3,6-tri-O-benzyl-beta -D-galactopyranosyl)-(1 -->4)-2,3,6-tri-O-benzyl-beta -D-glucopyranoside (8) and the corresponding III3-levulinoyl derivative (9), were regioselectively glycosylated with the phenyl 2-thioglycoside of N-acetylneuraminic acid (Neu5Ac) promoted by N-iodosuccinimide (NIS)-trimethylsilyl trifluoromethanesulfonate (TMSOTf) or trifluoromethanesulfonic acid (TfOH) in acetonitrile, to give the desired alpha -Neu5Ac-(2-->6)-gangliotriose (III(6)Neu5AcGgOse3) derivatives as the major products (11 and 12). The p-methoxybenzyl (MPM) group in 11 or the levulinoyl group in 12 was selectively removed, and the resulting 2-(trimethylsilyl)ethyl (methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-alpha -D-galacto-2-nonulopyranosylonate)-(2-->6)-(2-acetamido-2-deoxy-beta -D-galactopyranosyl)-(1-->4)-(2,3,6-tri-O-benzyl-beta -D-galactopyranosyl)-(1-->4)-2,3,6-tri-O-benzyl-beta -D-glucopyranoside (13), a key glycosyl acceptor, was systematically glycosylated with the galactose donor (14), alpha -Neu5Ac-(2-->3)-galactuse donor (15) and alpha -Neu5Ac-(2-->8)-alpha -Neu5Ac-(2-->3)-galactose donor (20) to give the protected GM1 alpha (16, 70%), GD1 alpha (17, 80%) and GT1 alpha (21, 87%) oligosaccharides, respectively, which can be converted to the target gangliosides by the introduction of ceramide and then complete deprotection.