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 | 176095-80-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 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)-β-D-galactopyranosyl>-β-D-glucopyranoside
• 英文别名: 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；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-hydroxyoxan-2-yl]methyl 4-methoxybenzoate
• CAS: 176095-80-0
• 化学式: C₅₃H₅₆O₁₆Si
• 分子量: 977.104
• InChiKey: LTEDVXHEIGNCKC-MWHXOSDXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.33
• 重原子数：
  70
• 可旋转键数：
  23
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  198
• 氢给体数：
  1
• 氢受体数：
  16

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  2-(trimethylsilyl)ethyl 4-O-(4,6-O-p-methoxybenzylidene-β-D-galactopyranosyl)-β-D-glucopyranoside 在 palladium on activated charcoal 咪唑 、 4-二甲氨基吡啶 、 氢气 、 溶剂黄146 、 三苯基膦 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 吡啶 、 乙醇 、 乙酸乙酯 、 三乙胺 、 甲苯 、 乙腈 为溶剂， 反应 8.0h， 生成 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
  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

• DDQ-Mediated Oxidation of 4,6-<i>O</i>-Methoxybenzylidene-Protected Saccharides in the Presence of Various Nucleophiles:  Formation of 4-OH, 6-Cl, and 6-Br Derivatives
  作者：Zhiyuan Zhang、Göran Magnusson

  DOI：10.1021/jo952177v

  日期：1996.1.1

  Treatment of 4,6-O-p-methoxybenzylidene-protected pyranosidic mono- and disaccharides with 2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ), in the presence of a few equivalents of water, gave the corresponding 6- and 4-O-p-methoxybenzoates with unprotected hydroxyl groups in the 4- and 6-position in the ratio similar to 4:1 and in 85-98% yield. Dry conditions in the presence of halide salts gave the 6-deoxychloro and -bromo 4-O-p-methoxybenzoates exclusively, in >90% yield.
• 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.