diphenylmethyl 2β,3β-epithio-11-oxo-18β-olean-12-en-29-oate | 1234424-63-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: diphenylmethyl 2β,3β-epithio-11-oxo-18β-olean-12-en-29-oate
• CAS: 1234424-63-5
• 化学式: C₄₃H₅₄O₃S
• 分子量: 650.966
• InChiKey: UPIRSIXPQOUIKG-XMGKTJBJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.39
• 重原子数：
  47.0
• 可旋转键数：
  4.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  43.37
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  diphenylmethyl 2β,3β-epithio-11-oxo-18β-olean-12-en-29-oate 、 乙酸酐 在 对甲苯磺酸 、 溶剂黄146 作用下， 反应 2.0h， 以70%的产率得到diphenylmethyl 2β-acetylthio-3α-acetyloxy-11-oxo-18β-olean-12-en-29-oate
  参考文献：
  名称：

  Synthesis and crystal structures of ring A modified glycyrrhetinic acid derivatives derived from 2,3-oxirane and 2,3-thiirane intermediates

  摘要：

  A general method for the introduction of thiol groups at positions 1, 2, and 3 of glycyrrhetinic acid has been developed starting from a protected 2 alpha,3 alpha-oxido-derivative. Conversion into the corresponding 2 beta,3 beta-epithio-derivative was followed by ring-opening leading to either 2- or 3-substituted thio derivatives. Conversely, 3 alpha-configured allylic alcohol intermediates derived from the 2,3-epoxide provided efficient access to both diastereoisomeric 3-thio derivatives as well as 1 alpha-thio derivatives. The stereochemistry of the newly formed stereogenic centers was rigorously proven using X-ray crystallography. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.03.098
• 作为产物：
  描述：

  diphenylmethyl 2α,3α-oxo-11-oxo-18β-olean-12-en-29-oate 在 N,N-二甲基硫代甲酰胺 、 三氟乙酸 作用下， 以 甲苯 为溶剂， 反应 4.0h， 以80%的产率得到diphenylmethyl 2β,3β-epithio-11-oxo-18β-olean-12-en-29-oate
  参考文献：
  名称：

  Synthesis and crystal structures of ring A modified glycyrrhetinic acid derivatives derived from 2,3-oxirane and 2,3-thiirane intermediates

  摘要：

  A general method for the introduction of thiol groups at positions 1, 2, and 3 of glycyrrhetinic acid has been developed starting from a protected 2 alpha,3 alpha-oxido-derivative. Conversion into the corresponding 2 beta,3 beta-epithio-derivative was followed by ring-opening leading to either 2- or 3-substituted thio derivatives. Conversely, 3 alpha-configured allylic alcohol intermediates derived from the 2,3-epoxide provided efficient access to both diastereoisomeric 3-thio derivatives as well as 1 alpha-thio derivatives. The stereochemistry of the newly formed stereogenic centers was rigorously proven using X-ray crystallography. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.03.098