(2S,4S)-N-Cbz-4-azidoproline | 1155262-85-3

• 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: (2S,4S)-N-Cbz-4-azidoproline
• 英文别名: (2S,4S)-1-Cbz-4-azidopyrrolidine-2-carboxylic acid；(2S,4S)-4-azido-1-phenylmethoxycarbonylpyrrolidine-2-carboxylic acid
• CAS: 1155262-85-3
• 化学式: C₁₃H₁₄N₄O₄
• 分子量: 290.279
• InChiKey: MCMIVURICADVMC-QWRGUYRKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  81.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2S,4S)-N-Cbz-4-azidoproline 、 (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29%的产率得到tert-butyl (1S,3S,4S,5S,6R)-2-[(2S,4S)-4-azido-1-phenylmethoxycarbonylpyrrolidine-2-carbonyl]-5,6-dihydroxy-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
• 作为产物：
  描述：

  4(S)-azido-N-<(phenylmethoxy)carbonyl>-(S)-proline methyl ester 在 sodium hydroxide 、 水 、 甲酸 作用下， 以 甲醇 、 水 为溶剂， 以100%的产率得到(2S,4S)-N-Cbz-4-azidoproline
  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.