(1R,3S,4S)-3-azido-4-trimethylsilanyloxy-cyclopentane-1-carboxylic acid benzyl ester | 915098-59-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (1R,3S,4S)-3-azido-4-trimethylsilanyloxy-cyclopentane-1-carboxylic acid benzyl ester
• CAS: 915098-59-8
• 化学式: C₁₆H₂₃N₃O₃Si
• 分子量: 333.462
• InChiKey: OGJZKCQNRARHTC-ILXRZTDVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.04
• 重原子数：
  23.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  84.29
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (1R,3S,4S)-3-azido-4-trimethylsilanyloxy-cyclopentane-1-carboxylic acid benzyl ester 在 sodium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 生成 (1R,3S,4S)-3-azido-4-hydroxy-cyclopentane-1-carboxylic acid
  参考文献：
  名称：

  Improved synthesis of the valuable peptidomimetic intermediate 3-azido-4-hydroxy cyclopentanoic acid

  摘要：

  An improved synthesis of 3-azido-4-hydroxy cyclopentanoic acid 2 is presented. This molecule is useful as a synthetic scaffold for P-turn mimetics on solid phase, with the selectivity of the turns being dependent on the diastereomer employed. A high diastereo-selectivity in the synthesis of this molecule in solution is reported, which may then be attached to the solid phase for the synthesis of peptidomimetic libraries. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.07.001
• 作为产物：
  描述：

  benzyl cyclopent-3-enecarboxylate 在 (1R,2R)-(-)-[1,2-cyclohexanediamine-N,N’-bis(3,5-di-tertbutylsalicylidine)]chromium(III) chloride 间氯过氧苯甲酸 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 30.25h， 生成 (1R,3S,4S)-3-azido-4-trimethylsilanyloxy-cyclopentane-1-carboxylic acid benzyl ester
  参考文献：
  名称：

  Improved synthesis of the valuable peptidomimetic intermediate 3-azido-4-hydroxy cyclopentanoic acid

  摘要：

  An improved synthesis of 3-azido-4-hydroxy cyclopentanoic acid 2 is presented. This molecule is useful as a synthetic scaffold for P-turn mimetics on solid phase, with the selectivity of the turns being dependent on the diastereomer employed. A high diastereo-selectivity in the synthesis of this molecule in solution is reported, which may then be attached to the solid phase for the synthesis of peptidomimetic libraries. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.07.001