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

• 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-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-β-D-galactopyranosyl>-β-D-glucopyranoside
• 英文别名: Bn(-2)[Bn(-3)][Bn(-4)][Bn(-6)]Gal(a1-4)[Bz(-2)][Bz(-3)][Bz(4-OMe)(-6)]Gal(b1-4)[Bz(-2)][Bz(-3)]Qui(b)-O-EtTMS；[(2R,3S,4S,5R,6S)-4,5-dibenzoyloxy-6-[(2R,3R,4S,5R,6R)-4,5-dibenzoyloxy-2-methyl-6-(2-trimethylsilylethoxy)oxan-3-yl]oxy-3-[(2R,3R,4S,5S,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxyoxan-2-yl]methyl 4-methoxybenzoate
• 化学式: C₈₇H₉₀O₂₁Si
• 分子量: 1499.74
• InChiKey: AYLGOXYYESVVDG-FOGATLBZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  14.05
• 重原子数：
  109
• 可旋转键数：
  38
• 环数：
  12.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  233
• 氢给体数：
  0
• 氢受体数：
  21

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-(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
• 作为产物：
  描述：

  (2R,3S,4S,5R,6R)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-6-chloro-tetrahydro-pyran 、 2-(trimethylsilyl)ethyl 2,3-di-O-benzoyl-6-deoxy-4-O-<2,3-di-O-benzoyl-6-O-(p-methoxybenzoyl)-β-D-galactopyranosyl>-β-D-glucopyranoside 在 2,3,5-三甲基吡啶 、 silver trifluoromethanesulfonate 作用下， 以 二氯甲烷 为溶剂， 以76%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-(2,3,4,6-tetra-O-benzyl-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

文献信息

• Synthesis of Double-Chain Bis-Sulfone Neoglycolipids of the 2-, 3-, and 6-Deoxyglobotrioses
  作者：Zhiyuan Zhang、Göran Magnusson

  DOI：10.1021/jo951914k

  日期：1996.1.1

  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.