(2R,3S)-3-Acetylamino-2-azidomethyl-5-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester | 515863-26-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (2R,3S)-3-Acetylamino-2-azidomethyl-5-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester
• 英文别名: tert-butyl (2R,3S)-3-acetamido-2-(azidomethyl)-5-oxopyrrolidine-1-carboxylate
• CAS: 515863-26-0
• 化学式: C₁₂H₁₉N₅O₄
• 分子量: 297.314
• InChiKey: UPBWHGYMEJEVOC-DTWKUNHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  90.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2R,3S)-3-Acetylamino-2-azidomethyl-5-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 48.0h， 以96%的产率得到((3R,4S)-4-Acetylamino-6-oxo-piperidin-3-yl)-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Diastereoselective synthesis of enantiopure differentially protected cis-4,5-diaminopiperidin-2-one through intramolecular transamidation

  摘要：

  The diastereoselective synthesis of enantiopure differentially protected cis-4,5-diaminopiperidin-2-one was achieved by means of conjugate addition of ammonia to an unsaturated gamma-lactam and transamidation reaction with ring expansion as the main steps. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)02418-8
• 作为产物：
  描述：

  Methanesulfonic acid (2S,3S)-3-acetylamino-5-oxo-pyrrolidin-2-ylmethyl ester 在 4-二甲氨基吡啶 、 sodium azide 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 生成 (2R,3S)-3-Acetylamino-2-azidomethyl-5-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Diastereoselective synthesis of enantiopure differentially protected cis-4,5-diaminopiperidin-2-one through intramolecular transamidation

  摘要：

  The diastereoselective synthesis of enantiopure differentially protected cis-4,5-diaminopiperidin-2-one was achieved by means of conjugate addition of ammonia to an unsaturated gamma-lactam and transamidation reaction with ring expansion as the main steps. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)02418-8

文献信息

• Diastereoselective synthesis of enantiopure differentially protected cis-4,5-diaminopiperidin-2-one through intramolecular transamidation
  作者：Nicole Langlois

  DOI：10.1016/s0040-4039(02)02418-8

  日期：2002.12

  The diastereoselective synthesis of enantiopure differentially protected cis-4,5-diaminopiperidin-2-one was achieved by means of conjugate addition of ammonia to an unsaturated gamma-lactam and transamidation reaction with ring expansion as the main steps. (C) 2002 Elsevier Science Ltd. All rights reserved.