tert-butyl (1S,3S,4S,5S,6R)-5,6-dihydroxy-2-[(2S)-1-phenylmethoxycarbonylpyrrolidine-2-carbonyl]-2-azabicyclo[2.2.1]heptane-3-carboxylate | 1155262-70-6

• 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: tert-butyl (1S,3S,4S,5S,6R)-5,6-dihydroxy-2-[(2S)-1-phenylmethoxycarbonylpyrrolidine-2-carbonyl]-2-azabicyclo[2.2.1]heptane-3-carboxylate
• CAS: 1155262-70-6
• 化学式: C₂₄H₃₂N₂O₇
• 分子量: 460.527
• InChiKey: FNYGCERDEGLQSA-RPZLJYRGSA-N

物化性质

• 沸点：
  629.1±55.0 °C(predicted)
• 密度：
  1.343±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  33
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  117
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  tert-butyl (1S,3S,4S,5S,6R)-5,6-dihydroxy-2-[(2S)-1-phenylmethoxycarbonylpyrrolidine-2-carbonyl]-2-azabicyclo[2.2.1]heptane-3-carboxylate 在 sodium periodate 、 水 作用下， 以 丙酮 为溶剂， 反应 2.5h， 生成
  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：

  N-苄氧羰基-L-脯氨酸 、 (1S,3S,4S,5S,6R)-5,6-dihydroxy-2-azabicyclo[2.2.1]heptane-3-carboxylic acid tert-butyl ester 在 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以91%的产率得到tert-butyl (1S,3S,4S,5S,6R)-5,6-dihydroxy-2-[(2S)-1-phenylmethoxycarbonylpyrrolidine-2-carbonyl]-2-azabicyclo[2.2.1]heptane-3-carboxylate
  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