ethyl (Z)-4-[tert-butyl(diphenyl)silyl]oxy-3-[(4R,5S)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-1,3-dioxolan-4-yl]but-2-enoate | 1147271-07-5

• 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: ethyl (Z)-4-[tert-butyl(diphenyl)silyl]oxy-3-[(4R,5S)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-1,3-dioxolan-4-yl]but-2-enoate
• CAS: 1147271-07-5
• 化学式: C₃₂H₄₄O₇Si
• 分子量: 568.783
• InChiKey: HRMWUKJRHWRJND-MUINOUHZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.72
• 重原子数：
  40
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  72.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  ethyl (Z)-4-[tert-butyl(diphenyl)silyl]oxy-3-[(4R,5S)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-1,3-dioxolan-4-yl]but-2-enoate 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以70%的产率得到
  参考文献：
  名称：

  Stereoselective synthesis of (+)-secosyrin 1

  摘要：

  A Chiron approach for the synthesis of (+)-secosyrin 1 from D-mannitol has been described. The key steps are a stereoselective Wittig reaction and an intramolecular Michael addition on the disubstituted butenolide, leading to a highly stereoselective formation of the tertiary chiral centre of (+)-secosyrin 1. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.01.106
• 作为产物：
  描述：

  2-(tert-butyldiphenylsilyloxy)-1-((4R,4'R,5S)-2,2,2',2'-tetramethyl-4,4'-bi(1,3-dioxolan)-5-yl)ethanone 、 乙氧甲酰基亚甲基三苯基膦 以 甲苯 为溶剂， 反应 5.0h， 以78%的产率得到ethyl (Z)-4-[tert-butyl(diphenyl)silyl]oxy-3-[(4R,5S)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-1,3-dioxolan-4-yl]but-2-enoate
  参考文献：
  名称：

  Stereoselective synthesis of (+)-secosyrin 1

  摘要：

  A Chiron approach for the synthesis of (+)-secosyrin 1 from D-mannitol has been described. The key steps are a stereoselective Wittig reaction and an intramolecular Michael addition on the disubstituted butenolide, leading to a highly stereoselective formation of the tertiary chiral centre of (+)-secosyrin 1. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.01.106

文献信息

• Stereoselective synthesis of (+)-secosyrin 1
  作者：D. Gautam、B. Venkateswara Rao

  DOI：10.1016/j.tetlet.2009.01.106

  日期：2009.4

  A Chiron approach for the synthesis of (+)-secosyrin 1 from D-mannitol has been described. The key steps are a stereoselective Wittig reaction and an intramolecular Michael addition on the disubstituted butenolide, leading to a highly stereoselective formation of the tertiary chiral centre of (+)-secosyrin 1. (C) 2009 Elsevier Ltd. All rights reserved.