6'-O-(tri-O-methylgalloyl)-2,3,4,6,1',3',4'-hepta-O-benzoylsucrose

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 单宁
• 英文名称: 6'-O-(tri-O-methylgalloyl)-2,3,4,6,1',3',4'-hepta-O-benzoylsucrose
• 英文别名: [(2R,3R,4S,5S)-3,4-dibenzoyloxy-5-(benzoyloxymethyl)-5-[(2R,3R,4S,5R,6R)-3,4,5-tribenzoyloxy-6-(benzoyloxymethyl)oxan-2-yl]oxyoxolan-2-yl]methyl 3,4,5-trimethoxybenzoate
• 化学式: C₇₁H₆₀O₂₂
• 分子量: 1265.24
• InChiKey: XAGZECJWYYKDTK-GUDBBUFISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.2
• 重原子数：
  93
• 可旋转键数：
  32
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  266
• 氢给体数：
  0
• 氢受体数：
  22

反应信息

• 作为产物：
  描述：

  6'-O-tert-butyldiphenylsilyl-2,3,4,6,1',3',4'-hepta-O-benzoylsucrose 在 四甲基乙二胺 、 3 A molecular sieve 、 溴 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 6'-O-(tri-O-methylgalloyl)-2,3,4,6,1',3',4'-hepta-O-benzoylsucrose
  参考文献：
  名称：

  Fast Galloylation of a Sugar Moiety: Preparation of Three Monogalloylsucroses as References for Antioxidant Activity. A Method for the Selective Deprotection of tert-Butyldiphenylsilyl Ethers

  摘要：

  Three protected new gallotannins, namely the 6'-O-(tri-O-methylgalloyl)-2,3,4,6,1',3',4'-hepta-O-acetylsucrose, the 6'-O-(tri-O-methylgalloyl)-2,3,4,6,1',3',4'-hepta-O-benzoylsucrose and the 6,6'-di-O-tert-butyldiphenylsilyl-1'-O-(tri-O-methylgalloyl)-2,3,4,3',4'-penta-O-acetylsucrose have been prepared in four short sequences from sucrose. Methods for rapid galloylation have been studied in order to avoid simultaneous acyl transfer reactions. A method for the deprotection of a tert-butyldiphenylsilyl ether has been developed which avoids the intramolecular migration of a benzoate group. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00593-7