(E,1S,8R)-8-[tert-butyl(diphenyl)silyl]oxy-1-[(3R)-1,4-dioxaspiro[4.5]decan-3-yl]non-3-en-1-ol | 1174761-24-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (E,1S,8R)-8-[tert-butyl(diphenyl)silyl]oxy-1-[(3R)-1,4-dioxaspiro[4.5]decan-3-yl]non-3-en-1-ol
• CAS: 1174761-24-0
• 化学式: C₃₃H₄₈O₄Si
• 分子量: 536.827
• InChiKey: XIHBXAZMJWHJOK-XHVLFFPVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  38
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E,1S,8R)-8-[tert-butyl(diphenyl)silyl]oxy-1-[(3R)-1,4-dioxaspiro[4.5]decan-3-yl]non-3-en-1-ol 、 叔丁基二苯基氯硅烷 在 咪唑 、 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 7.0h， 以88%的产率得到
  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：

  (R)-tert-butyl(hept-6-en-2-yloxy)diphenylsilane 、 1(S)-[(2R)-1,4-dioxaspiro[4.5]decanyl]-3-buten-1-ol 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以63%的产率得到(E,1S,8R)-8-[tert-butyl(diphenyl)silyl]oxy-1-[(3R)-1,4-dioxaspiro[4.5]decan-3-yl]non-3-en-1-ol
  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.