ethyl (3S,4S)-5-(tert-butyldiphenylsilanyloxy)-3,4-dimethyl-pentanoate | 1188416-78-5

• 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 (3S,4S)-5-(tert-butyldiphenylsilanyloxy)-3,4-dimethyl-pentanoate
• 英文别名: ethyl (3S,4S)-5-[tert-butyl(diphenyl)silyl]oxy-3,4-dimethylpentanoate
• CAS: 1188416-78-5
• 化学式: C₂₅H₃₆O₃Si
• 分子量: 412.645
• InChiKey: FVDMLHMTFFOYDV-LEWJYISDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.79
• 重原子数：
  29
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.48
• 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 (3S,4S)-5-(tert-butyldiphenylsilanyloxy)-3,4-dimethyl-pentanoate 在 二异丁基氢化铝 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 (3S,4S)-5-((tert-butyldiphenylsilyl)oxy)-3,4-dimethylpentanal
  参考文献：
  名称：

  Synthesis of Vicinal Dimethyl Chirons by Asymmetric Hydrogenation of Trisubstituted Alkenes

  摘要：

  Roche ester derivatives were converted to trisubstituted alkenes with allylic chiral centers. Hydrogenation of these substrates with chiral analogues of Crabtree's catalyst, specifically, an optically active carbene oxazoline derivative, were found to be mostly catalyst controlled. However, the peripheral functionalities and protecting groups had significant effects and could be adjusted to give high stereoselectivities. The upshot of this work is that alpha,omega-functionalized chirons to introduce 1,2-dimethyl functionalities into acyclic chains have been developed.

  DOI：

  10.1021/ja905458n
• 作为产物：
  描述：

  ethyl (2E,4S)-5-(tert-butyldiphenylsilanyloxy)-3,4-dimethyl-pent-2-enoate 在 [C₈H₁₂IrC₁₀H₁₅C₃H₃ONCH₂CH₂N₂C₃H₃C₆H₃C₆H₁₄]⁽¹⁺⁾*B(C₆H₃(CF₃)2)4^(1-)=[C₈H₁₂IrC₁₀H₁₅C₃H₃ONCH₂CH₂N₂C₃H₃C₆H₃C₆H₁₄]B(C₆H₃C₂F₆)4 、 氢气 作用下， 以 二氯甲烷 为溶剂， 25.0 ℃ 、5.0 MPa 条件下， 反应 6.0h， 生成 ethyl (3S,4S)-5-(tert-butyldiphenylsilanyloxy)-3,4-dimethyl-pentanoate
  参考文献：
  名称：

  Synthesis of Vicinal Dimethyl Chirons by Asymmetric Hydrogenation of Trisubstituted Alkenes

  摘要：

  Roche ester derivatives were converted to trisubstituted alkenes with allylic chiral centers. Hydrogenation of these substrates with chiral analogues of Crabtree's catalyst, specifically, an optically active carbene oxazoline derivative, were found to be mostly catalyst controlled. However, the peripheral functionalities and protecting groups had significant effects and could be adjusted to give high stereoselectivities. The upshot of this work is that alpha,omega-functionalized chirons to introduce 1,2-dimethyl functionalities into acyclic chains have been developed.

  DOI：

  10.1021/ja905458n

文献信息

• Synthesis of Vicinal Dimethyl Chirons by Asymmetric Hydrogenation of Trisubstituted Alkenes
  作者：Jian Zhao、Kevin Burgess

  DOI：10.1021/ja905458n

  日期：2009.9.23

  Roche ester derivatives were converted to trisubstituted alkenes with allylic chiral centers. Hydrogenation of these substrates with chiral analogues of Crabtree's catalyst, specifically, an optically active carbene oxazoline derivative, were found to be mostly catalyst controlled. However, the peripheral functionalities and protecting groups had significant effects and could be adjusted to give high stereoselectivities. The upshot of this work is that alpha,omega-functionalized chirons to introduce 1,2-dimethyl functionalities into acyclic chains have been developed.