(2S,9R)-2,9-di-(tert-butyldiphenylsilyloxy)dec-4E-enal | 1174761-27-3

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (2S,9R)-2,9-di-(tert-butyldiphenylsilyloxy)dec-4E-enal
• 英文别名: (E,2S,9R)-2,9-bis[[tert-butyl(diphenyl)silyl]oxy]dec-4-enal
• CAS: 1174761-27-3
• 化学式: C₄₂H₅₄O₃Si₂
• 分子量: 663.06
• InChiKey: ZENWQCRQGYRBDU-CMFULLSDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.21
• 重原子数：
  47
• 可旋转键数：
  17
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  (2R,3S,10R)-3,10-di-(tert-butyldiphenylsilyloxy)undec-5E-ene-1,2-diol 在 sodium periodate 作用下， 以 水 、 乙腈 为溶剂， 反应 1.0h， 以91%的产率得到(2S,9R)-2,9-di-(tert-butyldiphenylsilyloxy)dec-4E-enal
  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.