2-(trimethylsilyl)ethyl 2,3-di-O-benzoyl-4,6-O-(p-methoxybenzylidene)-β-D-glucopyranoside

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃二恶英
• 英文名称: 2-(trimethylsilyl)ethyl 2,3-di-O-benzoyl-4,6-O-(p-methoxybenzylidene)-β-D-glucopyranoside
• 英文别名: [(4aR,6R,7R,8S,8aR)-7-benzoyloxy-2-(4-methoxyphenyl)-6-(2-trimethylsilylethoxy)-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-8-yl] benzoate
• 化学式: C₃₃H₃₈O₉Si
• 分子量: 606.745
• InChiKey: GOJFJMGLRRUZNK-ZREQEOPLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.64
• 重原子数：
  43
• 可旋转键数：
  12
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  98.8
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  2-(trimethylsilyl)ethyl 2,3-di-O-benzoyl-4,6-O-(p-methoxybenzylidene)-β-D-glucopyranoside 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 水 、 乙腈 为溶剂， 反应 6.0h， 以96%的产率得到2-(trimethylsilyl)ethyl 2,3-di-O-benzoyl-β-D-glucopyranoside
  参考文献：
  名称：

  DDQ-Mediated Oxidation of 4,6-O-Methoxybenzylidene-Protected Saccharides in the Presence of Various Nucleophiles:  Formation of 4-OH, 6-Cl, and 6-Br Derivatives

  摘要：

  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.

  DOI：

  10.1021/jo952177v
• 作为产物：
  描述：

  2-(trimethylsilyl)ethyl β-D-glucopyranoside 在 对甲苯磺酸 、 三乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 4.0h， 生成 2-(trimethylsilyl)ethyl 2,3-di-O-benzoyl-4,6-O-(p-methoxybenzylidene)-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.
• 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.