ethyl (R,E)-4-[(tert-butyldiphenylsiloxy)methyl]-2-methylhex-2-enoate | 1629189-45-2

• 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 (R,E)-4-[(tert-butyldiphenylsiloxy)methyl]-2-methylhex-2-enoate
• 英文别名: ethyl (E,4R)-4-[[tert-butyl(diphenyl)silyl]oxymethyl]-2-methylhex-2-enoate
• CAS: 1629189-45-2
• 化学式: C₂₆H₃₆O₃Si
• 分子量: 424.656
• InChiKey: IBPGKAKBNMJKBA-SNJAAQEYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  30
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 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：

  ethyl (R,E)-4-[(tert-butyldiphenylsiloxy)methyl]-2-methylhex-2-enoate 在 二异丁基氢化铝 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 1.83h， 以88%的产率得到(R,E)-4-[(tert-butyldiphenylsiloxy)methyl]-2-methylhex-2-en-1-ol
  参考文献：
  名称：

  Catalytic Enantioselective Total Synthesis of (–)-Pyridovericin

  摘要：

  The first enantioselective catalytic total synthesis of (-)-pyridovericin is reported. The key steps involve a modified HWE reaction under aqueous conditions and an asymmetric iridium-catalyzed hydrogenation. This resulted in a highly modular and stereoselective approach that delivered the target natural product in high yield and stereoselectivity.

  DOI：

  10.1055/s-0033-1340868
• 作为产物：
  描述：

  methyl (E)-2-[(tert-butyldimethylsiloxy)methyl]but-2-enoate 在 C₂₆H₂₂NOP*C₃₂H₁₂BF₂₄^(1-)*C₈H₁₂*Ir⁽¹⁺⁾ 、 氢气 、 二异丁基氢化铝 作用下， 以 二氯甲烷 为溶剂， -78.0~20.0 ℃ 、5.0 MPa 条件下， 反应 65.0h， 生成 ethyl (R,E)-4-[(tert-butyldiphenylsiloxy)methyl]-2-methylhex-2-enoate
  参考文献：
  名称：

  Catalytic Enantioselective Total Synthesis of (–)-Pyridovericin

  摘要：

  The first enantioselective catalytic total synthesis of (-)-pyridovericin is reported. The key steps involve a modified HWE reaction under aqueous conditions and an asymmetric iridium-catalyzed hydrogenation. This resulted in a highly modular and stereoselective approach that delivered the target natural product in high yield and stereoselectivity.

  DOI：

  10.1055/s-0033-1340868

文献信息

• Catalytic Enantioselective Total Synthesis of (–)-Pyridovericin
  作者：Karl Gademann、Fabian Schmid、Maurizio Bernasconi、Henning Jessen、Andreas Pfaltz

  DOI：10.1055/s-0033-1340868

  日期：——

  The first enantioselective catalytic total synthesis of (-)-pyridovericin is reported. The key steps involve a modified HWE reaction under aqueous conditions and an asymmetric iridium-catalyzed hydrogenation. This resulted in a highly modular and stereoselective approach that delivered the target natural product in high yield and stereoselectivity.