Methyl 8-benzyloxycarbonylamino-5(S)-tert-butyloxycarbonylamino-2-(indole-3-yl)methyl-2-methoxycarbonyl-4-oxooctanoate | 134935-91-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: Methyl 8-benzyloxycarbonylamino-5(S)-tert-butyloxycarbonylamino-2-(indole-3-yl)methyl-2-methoxycarbonyl-4-oxooctanoate
• 英文别名: 2-(6-Benzyloxycarbonylamino-3-tert-butoxycarbonylamino-2-oxo-hexyl)-2-(1H-indol-3-ylmethyl)-malonic acid dimethyl ester
• CAS: 134935-91-4
• 化学式: C₃₃H₄₁N₃O₉
• 分子量: 623.703
• InChiKey: NJIDCKPWRFHNKY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  45.0
• 可旋转键数：
  14.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  162.12
• 氢给体数：
  3.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  Methyl 8-benzyloxycarbonylamino-5(S)-tert-butyloxycarbonylamino-2-(indole-3-yl)methyl-2-methoxycarbonyl-4-oxooctanoate 在 palladium on activated charcoal sodium hydroxide 、 氢气 作用下， 以 1,4-二氧六环 为溶剂， 反应 1.0h， 生成 3-(3-tert-Butoxycarbonylamino-2-hydroxy-piperidin-2-yl)-2-(1H-indol-3-ylmethyl)-propionic acid
  参考文献：
  名称：

  A facile synthesis of 8-amino-3-oxoindolizidine derivatives as conformationally restricted ornithyl pseudodipeptides

  摘要：

  One pot procedure for the synthesis of 8-amino-3-oxoindolizidines from Z-delta-protected ornithyl ketomethylene pseudodipeptide derivatives is described. This procedure, involving hydrogenolysis of the Z-group, intramolecular reductive amination and gamma-lactamization, provides readily access to a variety of 3-oxoindolizidines of defined stereochemistry at C-8 and C-8a.

  DOI：

  10.1016/s0040-4039(00)74495-9
• 作为产物：
  描述：

  methiodide of gramine 、 2-(6-Benzyloxycarbonylamino-3-tert-butoxycarbonylamino-2-oxo-hexyl)-malonic acid dimethyl ester 在 sodium methylate 作用下， 以76%的产率得到Methyl 8-benzyloxycarbonylamino-5(S)-tert-butyloxycarbonylamino-2-(indole-3-yl)methyl-2-methoxycarbonyl-4-oxooctanoate
  参考文献：
  名称：

  A facile synthesis of 8-amino-3-oxoindolizidine derivatives as conformationally restricted ornithyl pseudodipeptides

  摘要：

  One pot procedure for the synthesis of 8-amino-3-oxoindolizidines from Z-delta-protected ornithyl ketomethylene pseudodipeptide derivatives is described. This procedure, involving hydrogenolysis of the Z-group, intramolecular reductive amination and gamma-lactamization, provides readily access to a variety of 3-oxoindolizidines of defined stereochemistry at C-8 and C-8a.

  DOI：

  10.1016/s0040-4039(00)74495-9