(E)-(4R,5S)-5-tert-Butoxycarbonylamino-4-hydroxy-hex-2-enoic acid methyl ester | 134210-23-4

• 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)-(4R,5S)-5-tert-Butoxycarbonylamino-4-hydroxy-hex-2-enoic acid methyl ester
• CAS: 134210-23-4
• 化学式: C₁₂H₂₁NO₅
• 分子量: 259.302
• InChiKey: JENULBNFTGTWKN-PUCWJLDJSA-N

反应信息

• 作为产物：
  描述：

  Acetic acid (R)-1-((S)-1-tert-butoxycarbonylamino-ethyl)-allyl ester 在 sodium carbonate 、 臭氧 、 三苯基膦 作用下， 以 甲醇 为溶剂， 生成 (E)-(4R,5S)-5-tert-Butoxycarbonylamino-4-hydroxy-hex-2-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