2-O-tert-butyl 3-O,5-O-dimethyl (2S,3S,5S)-1-[(2S,4S)-4-cyano-1-phenylmethoxycarbonylpyrrolidine-2-carbonyl]pyrrolidine-2,3,5-tricarboxylate | 1155262-92-2

• 英文名称: 2-O-tert-butyl 3-O,5-O-dimethyl (2S,3S,5S)-1-[(2S,4S)-4-cyano-1-phenylmethoxycarbonylpyrrolidine-2-carbonyl]pyrrolidine-2,3,5-tricarboxylate
• CAS: 1155262-92-2
• 化学式: C₂₇H₃₃N₃O₉
• 分子量: 543.574
• InChiKey: MUVGLSCLQQQGJH-SYAJIYQZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  39
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  153
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  2-O-tert-butyl 3-O,5-O-dimethyl (2S,3S,5S)-1-[(2S,4S)-4-cyano-1-phenylmethoxycarbonylpyrrolidine-2-carbonyl]pyrrolidine-2,3,5-tricarboxylate 在 palladium 10% on activated carbon 、 氢气 、 N,N-二异丙基乙胺 作用下， 以 甲醇 为溶剂， 以16%的产率得到6-O-tert-butyl 5-O-methyl (3S,5S,6S,9S,11R)-11-(aminomethyl)-2,8-dioxo-1,7-diazatricyclo[7.3.0.03,7]dodecane-5,6-dicarboxylate
  参考文献：
  名称：

  Synthesis of Proline-Based Diketopiperazine Scaffolds

  摘要：

  A number of natural products with interesting biological properties are based on a diketopiperazine scaffold. In this context, we have developed a diversity oriented and efficient synthetic strategy to highly functionalized proline-based diketopiperazines. In this paper we describe the stereoselective synthesis of various scaffolds resembling abundant natural product core structures. These scaffolds can be conjugated to a solid phase and are thus platforms for the construction of small compound libraries and the synthesis of natural products with diketopiperazine cores.

  DOI：

  10.1021/jo9004876
• 作为产物：
  描述：

  、 三甲基硅烷化重氮甲烷 以 甲醇 、 乙醚 、 甲苯 为溶剂， 以0.15 g的产率得到2-O-tert-butyl 3-O,5-O-dimethyl (2S,3S,5S)-1-[(2S,4S)-4-cyano-1-phenylmethoxycarbonylpyrrolidine-2-carbonyl]pyrrolidine-2,3,5-tricarboxylate
  参考文献：
  名称：

  Synthesis of Proline-Based Diketopiperazine Scaffolds

  摘要：

  A number of natural products with interesting biological properties are based on a diketopiperazine scaffold. In this context, we have developed a diversity oriented and efficient synthetic strategy to highly functionalized proline-based diketopiperazines. In this paper we describe the stereoselective synthesis of various scaffolds resembling abundant natural product core structures. These scaffolds can be conjugated to a solid phase and are thus platforms for the construction of small compound libraries and the synthesis of natural products with diketopiperazine cores.

  DOI：

  10.1021/jo9004876