methyl (6S,13R)-6,13-di-(tert-butyldiphenylsilyloxy)tetradeca-(2E,4E,8E)-trienoate | 1174761-28-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: methyl (6S,13R)-6,13-di-(tert-butyldiphenylsilyloxy)tetradeca-(2E,4E,8E)-trienoate
• 英文别名: methyl (2E,4E,6S,8E,13R)-6,13-bis[[tert-butyl(diphenyl)silyl]oxy]tetradeca-2,4,8-trienoate
• CAS: 1174761-28-4
• 化学式: C₄₇H₆₀O₄Si₂
• 分子量: 745.162
• InChiKey: MSJPEARWEQNGJW-PFVKUUMISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.3
• 重原子数：
  53
• 可旋转键数：
  20
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl (6S,13R)-6,13-di-(tert-butyldiphenylsilyloxy)tetradeca-(2E,4E,8E)-trienoate 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以87%的产率得到methyl (6S,13R)-6,13-dihydroxy-2E,4E,8E-tetradecatrienoate
  参考文献：
  名称：

  A chemoenzymatic asymmetric synthesis of methyl (6S,13R)-6,13-dihydroxytetradeca-(2E,4E,8E)-trienoate, a component of Mycosphaerella rubella

  摘要：

  The first asymmetric synthesis of (6S,13R)-6,13-dihydroxytetradeca-(2E,4E,8E)-trienoate has been developed. The key steps of the synthesis were the use of an efficient lipase-catalyzed acylation, a chiral template-driven enantiocontrolled allylation for introducing the stereogenic centers, and a cross-meta thesis for controlling the C-8 olefin geometry. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.04.004
• 作为产物：
  描述：

  (2S,9R)-2,9-di-(tert-butyldiphenylsilyloxy)dec-4E-enal 、 methyl 4-(diethylphosphono)crotonate 在 sodium hydride 作用下， 以 四氢呋喃 、 mineral oil 为溶剂， 反应 18.25h， 以79%的产率得到methyl (6S,13R)-6,13-di-(tert-butyldiphenylsilyloxy)tetradeca-(2E,4E,8E)-trienoate
  参考文献：
  名称：

  A chemoenzymatic asymmetric synthesis of methyl (6S,13R)-6,13-dihydroxytetradeca-(2E,4E,8E)-trienoate, a component of Mycosphaerella rubella

  摘要：

  The first asymmetric synthesis of (6S,13R)-6,13-dihydroxytetradeca-(2E,4E,8E)-trienoate has been developed. The key steps of the synthesis were the use of an efficient lipase-catalyzed acylation, a chiral template-driven enantiocontrolled allylation for introducing the stereogenic centers, and a cross-meta thesis for controlling the C-8 olefin geometry. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.04.004

文献信息

• A chemoenzymatic asymmetric synthesis of methyl (6S,13R)-6,13-dihydroxytetradeca-(2E,4E,8E)-trienoate, a component of Mycosphaerella rubella
  作者：Anubha Sharma、Sunita Gamre、Subrata Chattopadhyay

  DOI：10.1016/j.tetasy.2009.04.004

  日期：2009.6

  The first asymmetric synthesis of (6S,13R)-6,13-dihydroxytetradeca-(2E,4E,8E)-trienoate has been developed. The key steps of the synthesis were the use of an efficient lipase-catalyzed acylation, a chiral template-driven enantiocontrolled allylation for introducing the stereogenic centers, and a cross-meta thesis for controlling the C-8 olefin geometry. (C) 2009 Elsevier Ltd. All rights reserved.