(E)-(4R,5S)-4-Acetoxy-5-tert-butoxycarbonylamino-6-(tert-butyl-dimethyl-silanyloxy)-hex-2-enoic acid methyl ester | 134387-93-2

• 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: (E)-(4R,5S)-4-Acetoxy-5-tert-butoxycarbonylamino-6-(tert-butyl-dimethyl-silanyloxy)-hex-2-enoic acid methyl ester
• 英文别名: (E)-(4S,5S)-4-Acetoxy-5-tert-butoxycarbonylamino-6-(tert-butyl-dimethyl-silanyloxy)-hex-2-enoic acid methyl ester
• CAS: 134387-93-2
• 化学式: C₂₀H₃₇NO₇Si
• 分子量: 431.602
• InChiKey: USPFLPUPCLZVIS-WFPWZJHXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.56
• 重原子数：
  29.0
• 可旋转键数：
  8.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  100.16
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (E)-(4R,5S)-4-Acetoxy-5-tert-butoxycarbonylamino-6-(tert-butyl-dimethyl-silanyloxy)-hex-2-enoic acid methyl ester 在 sodium carbonate 作用下， 以 甲醇 为溶剂， 反应 20.0h， 生成 methyl (4S,5S,2E)-5-amino-6-(tert-butyldimethylsiloxy)-N-<(tert-butyloxy)carbonyl>-4-hydroxy-2-hexenoate
  参考文献：
  名称：

  A highly stereoselective synthesis of (E)-alkene dipeptide isosteres via organocyanocopper-Lewis acid mediation reaction

  摘要：

  A stereoselective synthesis of protected (E)-alkene dipeptide isosteres by the reaction of the mesylates of homochiral delta-aminated gamma-hydroxy (E)-alpha,beta-enoates with either RCu(CN)Li.BF3 or RCu(CN)MgX.BF3 reagent is described. The degree of diastereoselectivity has been found to be uniformly high except for the serine- and threonine-derived acetonides 77 and 81. The synthesis permits the introduction of sterically hindered appendages such as isopropyl and tert-butyl groups at the alpha position to the ester group. This methodology provides a new route to a wide range of modified (E)-alkene peptide mimics that may have biological importance.

  DOI：

  10.1021/jo00014a010