2-(trimethylsilyl)ethyl [methyl 5-acetamido-8-O-(5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylono-1',9-lactone)-4,7-di-O-acetyl-3,5-dideoxy-D-glycero-β-D-galacto-2-nonulopyranosylonate]-(2->3)-2,6-di-O-benzyl-β-D-galactopyranoside | 1139611-74-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(trimethylsilyl)ethyl [methyl 5-acetamido-8-O-(5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylono-1',9-lactone)-4,7-di-O-acetyl-3,5-dideoxy-D-glycero-β-D-galacto-2-nonulopyranosylonate]-(2->3)-2,6-di-O-benzyl-β-D-galactopyranoside
• 英文别名: methyl (2R,4S,5R,6R)-5-acetamido-6-[(S)-[(2R,6S,8R,9R,10S)-9-acetamido-10-acetyloxy-5-oxo-8-[(1S,2R)-1,2,3-triacetyloxypropyl]-1,4,7-trioxaspiro[5.5]undecan-2-yl]-acetyloxymethyl]-4-acetyloxy-2-[(2R,3S,4S,5R,6R)-3-hydroxy-5-phenylmethoxy-2-(phenylmethoxymethyl)-6-(2-trimethylsilylethoxy)oxan-4-yl]oxyoxane-2-carboxylate
• CAS: 1139611-74-7
• 化学式: C₆₀H₈₂N₂O₂₇Si
• 分子量: 1291.39
• InChiKey: JMUDZEMVQXDHQT-QCUMUWPFSA-N

物化性质

• 沸点：
  1140.1±65.0 °C(predicted)
• 密度：
  1.33±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.93
• 重原子数：
  90
• 可旋转键数：
  34
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  363
• 氢给体数：
  3
• 氢受体数：
  27

反应信息

• 作为产物：
  描述：

  2-(trimethylsilyl)ethyl 2,6-di-O-benzyl-β-D-galactopyranoside 、 methyl[phenyl 5-acetamido-8-O-(5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-ulopyranosylono-1',9-lactone)-4,7-di-O-acetyl-3,5-dideoxy-2-thio-D-glycero-D-galacto-non-2-ulopyranosid]onate 生成 2-(trimethylsilyl)ethyl [methyl 5-acetamido-8-O-(5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylono-1',9-lactone)-4,7-di-O-acetyl-3,5-dideoxy-D-glycero-β-D-galacto-2-nonulopyranosylonate]-(2->3)-2,6-di-O-benzyl-β-D-galactopyranoside 、 2-(trimethylsilyl)ethyl [methyl 5-acetamido-8-O-(5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylono-1',9-lactone)-4,7-di-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonate]-(2->3)-2,6-di-O-benzyl-β-D-galactopyranoside
  参考文献：
  名称：

  METHOD OF ALPHA-SELECTIVE GLYCOSYLATION

  摘要：

  公开号：

  EP1626053B1

文献信息

• Ganglioside GQ1b: Efficient Total Synthesis and the Expansion to Synthetic Derivatives To Elucidate Its Biological Roles
  作者：Akihiro Imamura、Hiromune Ando、Hideharu Ishida、Makoto Kiso

  DOI：10.1021/jo8027888

  日期：2009.4.17

  The convergent total synthesis of ganglioside GQ1b based on the “cassette approach” between the nonreducing end GQ1b-core heptasaccharide and glucosylceramide building blocks was accomplished in high overall yield. The use of a sialylα(2→8)sialylα(2→3)galactose sequence as the key building block enhanced the efficiency of the glycan assembly and led to preparative-scale synthesis readily applicable

  基于“盒式方法”，在非还原性末端GQ1b核心七糖和葡萄糖基神经酰胺结构单元之间实现了神经节苷脂GQ1b的聚合全合成，从而获得了较高的总收率。使用唾液酸基α（2→8）唾液酸基α（2→3）半乳糖序列作为关键构建基块提高了聚糖组装体的效率，并导致易于用于大规模制备的制备规模合成。另外，p的明智选择葡糖神经酰胺上的-甲氧基苄基保护基为先前的合成问题提供了解决方案，包括降低脱保护步骤的收率，并导致总收率的提高。此外，为了阐明其生物学作用，利用相似的方法系统地合成了高产率的非天然GQ1b衍生物。