methyl 6-O-(3-benzyloxy-2,2-bis(benzyloxymethyl)propanoyloxy)-α-D-glucopyranoside | 1309460-00-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 6-O-(3-benzyloxy-2,2-bis(benzyloxymethyl)propanoyloxy)-α-D-glucopyranoside
• 英文别名: [(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-methoxyoxan-2-yl]methyl 3-phenylmethoxy-2,2-bis(phenylmethoxymethyl)propanoate
• CAS: 1309460-00-1
• 化学式: C₃₃H₄₀O₁₀
• 分子量: 596.675
• InChiKey: OFWOLAAREHFBCQ-SAEUYMBFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  43
• 可旋转键数：
  17
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  133
• 氢给体数：
  3
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  3-(benzyloxy)-2,2-bis(benzyloxymethyl)propanoic acid 、 alpha-甲基葡萄糖甙 在 N,N-二异丙基乙胺 、 O‐(1H‐benzotriazol‐1‐yl)‐N,N,N′,N′‐tetramethyluronium tetrafluoroborate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 以78%的产率得到methyl 6-O-(3-benzyloxy-2,2-bis(benzyloxymethyl)propanoyloxy)-α-D-glucopyranoside
  参考文献：
  名称：

  Efficient and Controllably Selective Preparation of Esters Using Uronium-Based Coupling Agents

  摘要：

  Carboxylic acid esters can be prepared in excellent yields at room temperature from an acid and either a phenol or an aliphatic alcohol using Me peptide coupling reagents, TBTU, TATU, or COMU, in the presence of organic bases. Reactions using TBTU and TATU are faster but do not occur with tertiary alcohols. Selectivity between reaction with primary or secondary alcohols in diols and polyols can be achieved with choice of base and coupling agent.

  DOI：

  10.1021/ol201005s

文献信息

• Efficient and Controllably Selective Preparation of Esters Using Uronium-Based Coupling Agents
  作者：Jean-d’Amour K. Twibanire、T. Bruce Grindley

  DOI：10.1021/ol201005s

  日期：2011.6.17

  Carboxylic acid esters can be prepared in excellent yields at room temperature from an acid and either a phenol or an aliphatic alcohol using Me peptide coupling reagents, TBTU, TATU, or COMU, in the presence of organic bases. Reactions using TBTU and TATU are faster but do not occur with tertiary alcohols. Selectivity between reaction with primary or secondary alcohols in diols and polyols can be achieved with choice of base and coupling agent.