methyl (2S)-2-[(3S)-3-benzyl-2-oxo-3-(phenylmethoxycarbonylamino)pyrrolidin-1-yl]propanoate | 117162-08-0

• 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: methyl (2S)-2-[(3S)-3-benzyl-2-oxo-3-(phenylmethoxycarbonylamino)pyrrolidin-1-yl]propanoate
• CAS: 117162-08-0
• 化学式: C₂₃H₂₆N₂O₅
• 分子量: 410.47
• InChiKey: INMCXNBAWSLGDC-GAJHUEQPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  30
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  84.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl (2S)-2-[(3S)-3-benzyl-2-oxo-3-(phenylmethoxycarbonylamino)pyrrolidin-1-yl]propanoate 在 palladium 10% on activated carbon 、 氢气 作用下， 以 1,4-二氧六环 为溶剂， 反应 17.0h， 以95%的产率得到methyl (S)-2-((S)-3-amino-3-benzyl-2-oxopyrrolidin-1-yl)-propanoate
  参考文献：
  名称：

  Tetrahydroisoquinoline-Based Spirocyclic Lactam as a Type II′ β-Turn Inducing Peptide Mimetic

  摘要：

  We present here spirocyclic lactam derivatives, embodying D-Phe and L-Ala amino acids as the central core and acting as tetrapeptide and hexapeptide mimetics. An efficient route for their synthesis is demonstrated by using the strategic combination of Seebach's self-reproduction of chirality chemistry and the Pictet-Spengler condensation as key steps. The conformational behavior of peptide mimetics was Investigated by Molecular modeling, X-ray crystallography, NMR (solvent and temperature dependence), IR spectroscopy, and circular dichroism. All data suggest very stable and highly predictable type II' beta-turn conformations.

  DOI：

  10.1021/jo901480d
• 作为产物：
  描述：

  benzyl (2R,4S)-4-benzyl-2-tert-butyl-5-oxo-4-(2-oxoethyl)-oxazolidine-3-carboxylate 、 L-丙氨酸甲酯盐酸盐 在 sodium acetate 、 甲醇 、 sodium cyanoborohydride 、 1-羟基苯并三唑 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 16.75h， 以67%的产率得到methyl (2S)-2-[(3S)-3-benzyl-2-oxo-3-(phenylmethoxycarbonylamino)pyrrolidin-1-yl]propanoate
  参考文献：
  名称：

  Tetrahydroisoquinoline-Based Spirocyclic Lactam as a Type II′ β-Turn Inducing Peptide Mimetic

  摘要：

  We present here spirocyclic lactam derivatives, embodying D-Phe and L-Ala amino acids as the central core and acting as tetrapeptide and hexapeptide mimetics. An efficient route for their synthesis is demonstrated by using the strategic combination of Seebach's self-reproduction of chirality chemistry and the Pictet-Spengler condensation as key steps. The conformational behavior of peptide mimetics was Investigated by Molecular modeling, X-ray crystallography, NMR (solvent and temperature dependence), IR spectroscopy, and circular dichroism. All data suggest very stable and highly predictable type II' beta-turn conformations.

  DOI：

  10.1021/jo901480d