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

• 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-benzyl-4,6-O-p-methoxybenzylidene-β-D-galactopyranoside
• 英文别名: 2-[[(4aR,6R,7R,8S,8aS)-2-(4-methoxyphenyl)-7,8-bis(phenylmethoxy)-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-6-yl]oxy]ethyl-trimethylsilane
• 化学式: C₃₃H₄₂O₇Si
• 分子量: 578.778
• InChiKey: GAIURVQCGJFINW-TWQDBXCVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.36
• 重原子数：
  41
• 可旋转键数：
  12
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  64.6
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-(trimethylsilyl)ethyl 2,3-di-O-benzyl-4,6-O-p-methoxybenzylidene-β-D-galactopyranoside 在 三甲基溴硅烷 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 氯仿 为溶剂， 反应 2.0h， 以53%的产率得到2-(trimethylsilyl)ethyl 2-O-benzyl-6-bromo-6-deoxy-4-O-p-methoxybenzoyl-β-D-galactopyranoside
  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-(三甲基硅烷基)乙基beta-吡喃半乳糖苷 在 sodium hydride 、 对甲苯磺酸 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 1.0h， 生成 2-(trimethylsilyl)ethyl 2,3-di-O-benzyl-4,6-O-p-methoxybenzylidene-β-D-galactopyranoside
  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

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.