(4R,5R,E)-tert-butyl 5-(tert-butyldimethylsilyloxy)-4-((2-methoxyethoxy)methoxy)hex-2-enoate | 1206731-99-8

• 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: (4R,5R,E)-tert-butyl 5-(tert-butyldimethylsilyloxy)-4-((2-methoxyethoxy)methoxy)hex-2-enoate
• CAS: 1206731-99-8
• 化学式: C₂₀H₄₀O₆Si
• 分子量: 404.62
• InChiKey: SIKBXSRBBJLDBO-CSLLIFPHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  27.0
• 可旋转键数：
  11.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  63.22
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (4R,5R,E)-tert-butyl 5-(tert-butyldimethylsilyloxy)-4-((2-methoxyethoxy)methoxy)hex-2-enoate 在 platinum(IV) oxide 、 氢气 作用下， 以 乙酸乙酯 为溶剂， 20.0 ℃ 、275.8 kPa 条件下， 反应 4.0h， 以94%的产率得到(4R,5R)-tert-butyl 5-(tert-butyldimethylsilyloxy)-4-((2-methoxyethoxy)methoxy)hexanoate
  参考文献：
  名称：

  Studies directed toward the first total synthesis of acremodiol and acremonol

  摘要：

  Studies directed toward the synthesis of acremodiol and acremonol resulted in the synthesis of two macrodiolides 1, la, and 2 besides 3. The attempted synthesis of 1 and 2 confirmed that the absolute stereochemistry defined in the earlier report is incorrect. Compound I was synthesized by RCM-mediated macrocyclization. Attempted synthesis of 2 failed to give good yields in the cyclization, and la and 2 were synthesized by the Yamaguchi macrolactonization method. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.10.030
• 作为产物：
  描述：

  2-甲氧基乙氧基甲基氯 、 (4R,5R)-(E)-5-(t-butyl(dimethyl)silyloxy)-4-hydroxy-2-hexenoic acid tert-butyl ester 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以84%的产率得到(4R,5R,E)-tert-butyl 5-(tert-butyldimethylsilyloxy)-4-((2-methoxyethoxy)methoxy)hex-2-enoate
  参考文献：
  名称：

  Studies directed toward the first total synthesis of acremodiol and acremonol

  摘要：

  Studies directed toward the synthesis of acremodiol and acremonol resulted in the synthesis of two macrodiolides 1, la, and 2 besides 3. The attempted synthesis of 1 and 2 confirmed that the absolute stereochemistry defined in the earlier report is incorrect. Compound I was synthesized by RCM-mediated macrocyclization. Attempted synthesis of 2 failed to give good yields in the cyclization, and la and 2 were synthesized by the Yamaguchi macrolactonization method. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.10.030