methyl 3,4,5-trihydroxy-2-[(2R)-3-oxo-3-phenylmethoxy-2-(phenylmethoxycarbonylamino)propyl]sulfanyl-6-(2,3,4-trihydroxy-6-methoxycarbonylphenyl)benzoate

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 单宁
• 英文名称: methyl 3,4,5-trihydroxy-2-[(2R)-3-oxo-3-phenylmethoxy-2-(phenylmethoxycarbonylamino)propyl]sulfanyl-6-(2,3,4-trihydroxy-6-methoxycarbonylphenyl)benzoate
• 化学式: C₃₄H₃₁NO₁₄S
• 分子量: 709.684
• InChiKey: KXSJHWCCLCPZQW-FQEVSTJZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  50
• 可旋转键数：
  16
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  264
• 氢给体数：
  7
• 氢受体数：
  15

反应信息

• 作为产物：
  描述：

  没食子酸甲酯 在 邻四氯苯醌 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 4.0h， 生成 methyl 3,4,5-trihydroxy-2-[(2R)-3-oxo-3-phenylmethoxy-2-(phenylmethoxycarbonylamino)propyl]sulfanyl-6-(2,3,4-trihydroxy-6-methoxycarbonylphenyl)benzoate
  参考文献：
  名称：

  Ellagitannin Chemistry. The First Synthesis of Dehydrohexahydroxydiphenoate Esters from Oxidative Coupling of Unetherified Methyl Gallate

  摘要：

  A simple o-chloranil-mediated oxidative dimerization of methyl gallate in anhydrous ether furnishes a dimethyl dehydrohexahydroxydiphenoate (DHHDP) product as a pale yellow precipitate in good yield. This methyl gallate dehydrodimer rapidly rearranges in acetone to give a mixture of two additional DHHDP regioisomers. One of these species corresponds to the isomer of the dehydrohexahydroxydiphenoyl group commonly observed in dehydroellagitannin natural products. Sodium dithionite-mediated reduction of the initially formed dimethyl dehydrohexahydroxydiphenoate and/or its derived regioisomers efficiently furnishes dimethyl hexahydroxydiphenoate (HHDP). Addition of N-(carbobenzyloxy)-L-cysteine benzyl ester to dimethyl dehydrohexahydroxydiphenoate(s) in THF solution produces two diastereomeric S-S-cysteinyl derivatives of dimethyl hexahydroxydiphenoate.

  DOI：

  10.1021/jo971354k

文献信息

• Ellagitannin Chemistry. The First Synthesis of Dehydrohexahydroxydiphenoate Esters from Oxidative Coupling of Unetherified Methyl Gallate
  作者：Stéphane Quideau、Ken S. Feldman

  DOI：10.1021/jo971354k

  日期：1997.12.1

  A simple o-chloranil-mediated oxidative dimerization of methyl gallate in anhydrous ether furnishes a dimethyl dehydrohexahydroxydiphenoate (DHHDP) product as a pale yellow precipitate in good yield. This methyl gallate dehydrodimer rapidly rearranges in acetone to give a mixture of two additional DHHDP regioisomers. One of these species corresponds to the isomer of the dehydrohexahydroxydiphenoyl group commonly observed in dehydroellagitannin natural products. Sodium dithionite-mediated reduction of the initially formed dimethyl dehydrohexahydroxydiphenoate and/or its derived regioisomers efficiently furnishes dimethyl hexahydroxydiphenoate (HHDP). Addition of N-(carbobenzyloxy)-L-cysteine benzyl ester to dimethyl dehydrohexahydroxydiphenoate(s) in THF solution produces two diastereomeric S-S-cysteinyl derivatives of dimethyl hexahydroxydiphenoate.