2-(Trimethylsilyl)ethyl 4-O-<3,6-di-O-benzoyl-2-deoxy-4-O-(α-D-galactopyranosyl)-β-D-lyxo-hexopyranosyl>-β-D-glucopyranoside | 1053702-97-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(Trimethylsilyl)ethyl 4-O-<3,6-di-O-benzoyl-2-deoxy-4-O-(α-D-galactopyranosyl)-β-D-lyxo-hexopyranosyl>-β-D-glucopyranoside
• 英文别名: Gal(a1-4)[Bz(-3)][Bz(-6)]2-deoxy-D-lyxHex(b1-4)Glc(b)-O-EtTMS；[(2R,3R,4R,6S)-4-benzoyloxy-6-[(2R,3S,4R,5R,6R)-4,5-dihydroxy-2-(hydroxymethyl)-6-(2-trimethylsilylethoxy)oxan-3-yl]oxy-3-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]methyl benzoate
• CAS: 1053702-97-8
• 化学式: C₃₇H₅₂O₁₇Si
• 分子量: 796.895
• InChiKey: XOGNFOCWCCLTBY-FBXJIUIFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.45
• 重原子数：
  55
• 可旋转键数：
  17
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  250
• 氢给体数：
  7
• 氢受体数：
  17

反应信息

• 作为反应物：
  描述：

  2-(Trimethylsilyl)ethyl 4-O-<3,6-di-O-benzoyl-2-deoxy-4-O-(α-D-galactopyranosyl)-β-D-lyxo-hexopyranosyl>-β-D-glucopyranoside 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 6.0h， 以94%的产率得到2-(Trimethylsilyl)ethyl 4-O-<2-deoxy-4-O-(α-D-galactopyranosyl)-β-D-lyxo-hexopyranosyl>-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 deoxylactosides (deoxygenated in the 2-, 3-, and 6-positions of the galactose unit) were synthesized via various routes and glycosylated with 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 86-96% overall yield. Glycosylation of 3-(hexadecylsulfonyl)-2-[(hexadecylsulfonyl)methyl]propanol with the trisaccharidic trichloroacetimidates, in 37-68% yield, followed by removal of protecting groups, gave the title neoglycolipids.

  DOI：

  10.1021/jo00127a042
• 作为产物：
  描述：

  2-(Trimethylsilyl)ethyl 2,3,6-tri-O-benzyl-4-O-<3,6-di-O-benzoyl-2-deoxy-4-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-β-D-lyxo-hexopyranosyl>-β-D-glucopyranoside 在 palladium on activated charcoal 氢气 作用下， 以 溶剂黄146 为溶剂， 反应 10.0h， 以97%的产率得到2-(Trimethylsilyl)ethyl 4-O-<3,6-di-O-benzoyl-2-deoxy-4-O-(α-D-galactopyranosyl)-β-D-lyxo-hexopyranosyl>-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 deoxylactosides (deoxygenated in the 2-, 3-, and 6-positions of the galactose unit) were synthesized via various routes and glycosylated with 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 86-96% overall yield. Glycosylation of 3-(hexadecylsulfonyl)-2-[(hexadecylsulfonyl)methyl]propanol with the trisaccharidic trichloroacetimidates, in 37-68% yield, followed by removal of protecting groups, gave the title neoglycolipids.

  DOI：

  10.1021/jo00127a042