2-(trimethylsilyl)ethyl 2,3-di-O-benzoyl-6-deoxy-4-O-<2,3-di-O-benzoyl-6-O-(p-methoxybenzoyl)-4-O-(α-D-galactopyranosyl)-β-D-galactopyranosyl>-β-D-glucopyranoside | 176165-34-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(trimethylsilyl)ethyl 2,3-di-O-benzoyl-6-deoxy-4-O-<2,3-di-O-benzoyl-6-O-(p-methoxybenzoyl)-4-O-(α-D-galactopyranosyl)-β-D-galactopyranosyl>-β-D-glucopyranoside
• CAS: 176165-34-7
• 化学式: C₅₉H₆₆O₂₁Si
• 分子量: 1139.25
• InChiKey: JNVWZNGRDGXEHM-UNMZCUQTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.15
• 重原子数：
  81.0
• 可旋转键数：
  21.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  277.03
• 氢给体数：
  4.0
• 氢受体数：
  21.0

反应信息

• 作为反应物：
  描述：

  2-(trimethylsilyl)ethyl 2,3-di-O-benzoyl-6-deoxy-4-O-<2,3-di-O-benzoyl-6-O-(p-methoxybenzoyl)-4-O-(α-D-galactopyranosyl)-β-D-galactopyranosyl>-β-D-glucopyranoside 在 敌草隆 、 三氟乙酸 作用下， 以 吡啶 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 2,3-di-O-benzoyl-6-deoxy-4-O-<2,3-di-O-benzoyl-6-O-(p-methoxybenzoyl)-4-O-(2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl)-β-D-galactopyranosyl>-β-D-glucopyranosyl trichloroacetamidate
  参考文献：
  名称：

  Synthesis of Double-Chain Bis-Sulfone Neoglycolipids of the 2-, 3-, and 6-Deoxyglobotrioses

  摘要：

  Partially protected 2-(trimethylsilyl)ethyl 2- and 3-deoxyglucosides and 6-deoxylactoside were synthesised via various routes and glycosylated with galabiosyl and galactosyl donors to give the corresponding deoxytrisaccharides. Removal of the protecting groups gave the 2-(trimethylsilyl)ethyl 2-, 3-, and 6-deoxyglobotriosides. Transformation of the protected trisaccharides into trichloroacetimidates, via the corresponding hemiacetals, proceeded in similar to 80% overall yield. Glycosylation of 3-(hexadecylsulfonyl)-2-[(hexadecylsulfonyl)methyl]propanol with the trisaccharidic trichloroacetimidates, in 72-79% yield, followed by removal of protecting groups, gave the title neoglycolipids.

  DOI：

  10.1021/jo951914k
• 作为产物：
  描述：

  2-(trimethylsilyl)ethyl 2,3-di-O-benzoyl-6-deoxy-4-O-<2,3-di-O-benzoyl-6-O-(p-methoxybenzoyl)-4-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-β-D-galactopyranosyl>-β-D-glucopyranoside 在 palladium on activated charcoal 氢气 作用下， 以 溶剂黄146 为溶剂， 反应 2.0h， 以93%的产率得到2-(trimethylsilyl)ethyl 2,3-di-O-benzoyl-6-deoxy-4-O-<2,3-di-O-benzoyl-6-O-(p-methoxybenzoyl)-4-O-(α-D-galactopyranosyl)-β-D-galactopyranosyl>-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of Double-Chain Bis-Sulfone Neoglycolipids of the 2-, 3-, and 6-Deoxyglobotrioses

  摘要：

  Partially protected 2-(trimethylsilyl)ethyl 2- and 3-deoxyglucosides and 6-deoxylactoside were synthesised via various routes and glycosylated with galabiosyl and galactosyl donors to give the corresponding deoxytrisaccharides. Removal of the protecting groups gave the 2-(trimethylsilyl)ethyl 2-, 3-, and 6-deoxyglobotriosides. Transformation of the protected trisaccharides into trichloroacetimidates, via the corresponding hemiacetals, proceeded in similar to 80% overall yield. Glycosylation of 3-(hexadecylsulfonyl)-2-[(hexadecylsulfonyl)methyl]propanol with the trisaccharidic trichloroacetimidates, in 72-79% yield, followed by removal of protecting groups, gave the title neoglycolipids.

  DOI：

  10.1021/jo951914k