(E)-(2S,5R)-5-tert-Butoxycarbonylamino-6-(tert-butyl-dimethyl-silanyloxy)-2-isobutyl-hex-3-enoic acid methyl ester | 127882-38-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (E)-(2S,5R)-5-tert-Butoxycarbonylamino-6-(tert-butyl-dimethyl-silanyloxy)-2-isobutyl-hex-3-enoic acid methyl ester
• CAS: 127882-38-6
• 化学式: C₂₂H₄₃NO₅Si
• 分子量: 429.673
• InChiKey: ORVUDFMCUOBKJH-CONOYDDESA-N

反应信息

• 作为产物：
  描述：

  (E)-(4S,5S)-5-tert-Butoxycarbonylamino-6-(tert-butyl-dimethyl-silanyloxy)-4-methanesulfonyloxy-hex-2-enoic acid methyl ester 、 alkaline earth salt of/the/ methylsulfuric acid 以 四氢呋喃 为溶剂， 以94%的产率得到(E)-(2S,5R)-5-tert-Butoxycarbonylamino-6-(tert-butyl-dimethyl-silanyloxy)-2-isobutyl-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

文献信息

• Ibuka, Toshiro; Habashita, Hiromu; Funakoshi, Susumu, Angewandte Chemie, 1990, vol. 102, # 7, p. 816 - 818
  作者：Ibuka, Toshiro、Habashita, Hiromu、Funakoshi, Susumu、Fujii, Nobutaka、Oguchi, Yusaku、et al.

  DOI：——

  日期：——