(2S,3R)-5-oxo-2-(((1S,4aS,8as)-5,5,8a-trimethyl-2-methylenedecahydronaphthalen-1-yl)methyl)tetrahydrofuran-3-carboxylicacid | 1258319-13-9

• 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: (2S,3R)-5-oxo-2-(((1S,4aS,8as)-5,5,8a-trimethyl-2-methylenedecahydronaphthalen-1-yl)methyl)tetrahydrofuran-3-carboxylicacid
• CAS: 1258319-13-9
• 化学式: C₂₀H₃₀O₄
• 分子量: 334.456
• InChiKey: MKVQJVXZZQMBAE-TYNWYWJLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.19
• 重原子数：
  24.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  63.6
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  (R)-4-benzyl-3-((2S,3R)-5-oxo-2-(((1S,4aS,8as)-5,5,8a-trimethyl-2-methylenedecahydronaphthalen-1-yl)methyl)tetrahydrofuran-3-carbonyl)oxazolidin-2-one 在 双氧水 、 lithium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 3.0h， 以90%的产率得到(2S,3R)-5-oxo-2-(((1S,4aS,8as)-5,5,8a-trimethyl-2-methylenedecahydronaphthalen-1-yl)methyl)tetrahydrofuran-3-carboxylicacid
  参考文献：
  名称：

  A fast and straightforward route towards the synthesis of the lissoclimide class of anti-tumour agents

  摘要：

  The synthesis of the chiral core structure of the lissoclimide class of anti-tumour agents containing three rings including a chiral succinimide subunit and an exocyclic double bond has been investigated The compound 7 was obtained without the use of any protecting groups for the alcohol at C-12 via an asymmetric boron-mediated aldol addition as the key step to install the chiral centres of the rare succimmido methanol moiety This was followed by a sequence of lactonisation microwave-assisted amidation and imidation reactions (C) 2010 Elsevier Ltd All rights reserved

  DOI：

  10.1016/j.tet.2010.09.031