methyl (2S,5S,3E)-5-amino-N-<(tert-butyloxy)carbonyl>-2-methyl-3-hexenoate | 127882-36-4

• 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: methyl (2S,5S,3E)-5-amino-N-<(tert-butyloxy)carbonyl>-2-methyl-3-hexenoate
• 英文别名: methyl (E,2S,5S)-2-methyl-5-[(2-methylpropan-2-yl)oxycarbonylamino]hex-3-enoate
• CAS: 127882-36-4
• 化学式: C₁₃H₂₃NO₄
• 分子量: 257.33
• InChiKey: ICKCLGQDFORGBF-GOPXOUGQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.26
• 重原子数：
  18.0
• 可旋转键数：
  4.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  64.63
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  methyl (2S,5S,3E)-5-amino-N-<(tert-butyloxy)carbonyl>-2-methyl-3-hexenoate 在 二异丁基氢化铝 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 3.0h， 以80%的产率得到((E)-(1S,4S)-5-Hydroxy-1,4-dimethyl-pent-2-enyl)-carbamic acid tert-butyl 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
• 作为产物：
  描述：

  methyl (4S,5S,2E)-4-acetoxy-5-amino-N-<(tert-butyloxy)carbonyl>-2-hexenoate 在 吡啶 、 sodium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 为溶剂， 反应 36.5h， 生成 methyl (2S,5S,3E)-5-amino-N-<(tert-butyloxy)carbonyl>-2-methyl-3-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

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：——
• IBUKA, TOSHIRO;HABASHITA, HIROMU;FUNAKOSHI, SUSUMU;FUJII, NOBUTAKA;OGUCHI+, ANGEW. CHEM., 102,(1990) N, C. 816-818
  作者：IBUKA, TOSHIRO、HABASHITA, HIROMU、FUNAKOSHI, SUSUMU、FUJII, NOBUTAKA、OGUCHI+

  DOI：——

  日期：——