(E)-(2R,5S)-5-tert-Butoxycarbonylamino-2-tert-butyl-6-phenyl-hex-3-enoic acid methyl ester | 134210-49-4

• 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)-(2R,5S)-5-tert-Butoxycarbonylamino-2-tert-butyl-6-phenyl-hex-3-enoic acid methyl ester
• 英文别名: methyl (E,2R,5S)-2-tert-butyl-5-[(2-methylpropan-2-yl)oxycarbonylamino]-6-phenylhex-3-enoate
• CAS: 134210-49-4
• 化学式: C₂₂H₃₃NO₄
• 分子量: 375.508
• InChiKey: OJBJGHCTWUKKRV-JUWLWVHDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  27
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (E)-(4S,5S)-5-tert-Butoxycarbonylamino-4-methanesulfonyloxy-6-phenyl-hex-2-enoic acid methyl ester 、 alkaline earth salt of/the/ methylsulfuric acid 以 四氢呋喃 、 乙醚 为溶剂， 以89%的产率得到(E)-(2R,5S)-5-tert-Butoxycarbonylamino-2-tert-butyl-6-phenyl-hex-3-enoic acid methyl ester
  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