2(R)-Benzyl-8(S)-tert-butyloxycarbonylamino-3-oxo-8a(R)-indolizidine-2-carboxylate | 136846-36-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 英文名称: 2(R)-Benzyl-8(S)-tert-butyloxycarbonylamino-3-oxo-8a(R)-indolizidine-2-carboxylate
• 英文别名: Rywfxpimhwadgx-gckmjxcfsa-；(2R,8S,8aR)-2-benzyl-8-[(2-methylpropan-2-yl)oxycarbonylamino]-3-oxo-1,5,6,7,8,8a-hexahydroindolizine-2-carboxylic acid
• CAS: 136846-36-1
• 化学式: C₂₁H₂₈N₂O₅
• 分子量: 388.464
• InChiKey: RYWFXPIMHWADGX-GCKMJXCFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  95.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  N-叔丁氧羰基-N'-苄氧羰基-L-鸟氨酸 在 palladium on activated charcoal sodium hydroxide 、 氢气 、 sodium methylate 、 sodium iodide 作用下， 以 甲醇 、 乙二醇二甲醚 为溶剂， 25.0 ℃ 、206.84 kPa 条件下， 反应 4.25h， 生成 2(R)-Benzyl-8(S)-tert-butyloxycarbonylamino-3-oxo-8a(R)-indolizidine-2-carboxylate
  参考文献：
  名称：

  Synthesis of 2-substituted 8-amino-3-oxoindolizidine-2-carboxylic acid derivatives as peptide conformation mimetics

  摘要：

  The synthesis of methyl 8-tert-butyloxycarbonylamino-3-oxoindolizidine-2-carboxylate and its alkyl derivatives bearing Phe, Trp and Asp side chains at C2 position are described. These bridged bicyclic lactams, obtained with high and moderate stereocontrol at C-8a and C2, respectively, have appropriate N- and C-protecting groups making them suitable for incorporation as spacers into higher peptides.

  DOI：

  10.1016/s0040-4020(01)90127-9

文献信息

• Synthesis of 2-substituted 8-amino-3-oxoindolizidine-2-carboxylic acid derivatives as peptide conformation mimetics
  作者：Rosario González-Muñiz、María José Domínguez、María Teresa García-López

  DOI：10.1016/s0040-4020(01)90127-9

  日期：1992.1

  The synthesis of methyl 8-tert-butyloxycarbonylamino-3-oxoindolizidine-2-carboxylate and its alkyl derivatives bearing Phe, Trp and Asp side chains at C2 position are described. These bridged bicyclic lactams, obtained with high and moderate stereocontrol at C-8a and C2, respectively, have appropriate N- and C-protecting groups making them suitable for incorporation as spacers into higher peptides.