(E)-(2R,5R)-5-tert-Butoxycarbonylamino-6-(tert-butyl-dimethyl-silanyloxy)-2-methyl-hex-3-enoic acid methyl ester | 127882-41-1

• 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,5R)-5-tert-Butoxycarbonylamino-6-(tert-butyl-dimethyl-silanyloxy)-2-methyl-hex-3-enoic acid methyl ester
• CAS: 127882-41-1
• 化学式: C₁₉H₃₇NO₅Si
• 分子量: 387.592
• InChiKey: FWHFXZJRWPOHRP-KPWZGGAESA-N

反应信息

• 作为产物：
  描述：

  methyl (E,4R,5S)-6-[tert-butyl(dimethyl)silyl]oxy-5-[(2-methylpropan-2-yl)oxycarbonylamino]-4-methylsulfonyloxyhex-2-enoate 、 alkaline earth salt of/the/ methylsulfuric acid 以 四氢呋喃 、 乙醚 为溶剂， 反应 0.5h， 以91%的产率得到(E)-(2R,5R)-5-tert-Butoxycarbonylamino-6-(tert-butyl-dimethyl-silanyloxy)-2-methyl-hex-3-enoic acid methyl ester
  参考文献：
  名称：

  Ibuka, Toshiro; Habashita, Hiromu; Funakoshi, Susumu, Angewandte Chemie, 1990, vol. 102, # 7, p. 816 - 818

  摘要：

  DOI：

文献信息

• A highly stereoselective synthesis of (E)-alkene dipeptide isosteres via organocyanocopper-Lewis acid mediation reaction
  作者：Toshiro Ibuka、Hiromu Habashita、Akira Otaka、Nobutaka Fujii、Yusaku Oguchi、Tadao Uyehara、Yoshinori Yamamoto

  DOI：10.1021/jo00014a010

  日期：1991.7

  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.