2-O-tert-butyl 3-O,5-O-dimethyl (2S,3S,5S)-1-[(2S)-1-phenylmethoxycarbonylpyrrolidine-2-carbonyl]pyrrolidine-2,3,5-tricarboxylate | 1155262-75-1

• 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: 2-O-tert-butyl 3-O,5-O-dimethyl (2S,3S,5S)-1-[(2S)-1-phenylmethoxycarbonylpyrrolidine-2-carbonyl]pyrrolidine-2,3,5-tricarboxylate
• CAS: 1155262-75-1
• 化学式: C₂₆H₃₄N₂O₉
• 分子量: 518.564
• InChiKey: XRPZVQZYISONGF-MUGJNUQGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  37
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  129
• 氢给体数：
  0
• 氢受体数：
  9

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)-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100%的产率得到6-O-tert-butyl 5-O-methyl (3S,5S,6S,9S)-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：

  (2S,4S,5S)-5-[(2-methylpropan-2-yl)oxycarbonyl]-1-[(2S)-1-phenylmethoxycarbonylpyrrolidine-2-carbonyl]pyrrolidine-2,4-dicarboxylic acid 、 三甲基硅烷化重氮甲烷 以 甲醇 、 乙醚 、 甲苯 为溶剂， 以3.01 g的产率得到2-O-tert-butyl 3-O,5-O-dimethyl (2S,3S,5S)-1-[(2S)-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

文献信息

• Synthesis of Proline-Based Diketopiperazine Scaffolds
  作者：N. Deppermann、A. H. G. P. Prenzel、A. Beitat、W. Maison

  DOI：10.1021/jo9004876

  日期：2009.6.5

  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.