(2R,3R,4R,5S)-2-(tert-Butoxycarbonylamino-methyl)-5-cyanomethyl-3,4-dihydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester | 188019-32-1

• 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,3R,4R,5S)-2-(tert-Butoxycarbonylamino-methyl)-5-cyanomethyl-3,4-dihydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester
• 英文别名: tert-butyl (2S,3R,4R,5R)-2-(cyanomethyl)-3,4-dihydroxy-5-[[(2-methylpropan-2-yl)oxycarbonylamino]methyl]pyrrolidine-1-carboxylate
• CAS: 188019-32-1
• 化学式: C₁₇H₂₉N₃O₆
• 分子量: 371.434
• InChiKey: WQLUZOJHWGQGOF-UMSGYPCISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  132
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 (2R,3R,4R,5S)-2-(tert-Butoxycarbonylamino-methyl)-5-cyanomethyl-3,4-dihydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 (2R,3R,4R,5S)-3,4-Diacetoxy-2-(tert-butoxycarbonylamino-methyl)-5-cyanomethyl-pyrrolidine-1-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Intramolecular cyclization of C2 symmetric and meso-iodo amino alcohols: A synthetic approach to azasugars

  摘要：

  C-2 Symmetric and meso-iodo hydroxy ammonium chlorides generated from 2 and 5 have been cyclized under basic conditions to produce various heterocycles chemoselectively, which comprise tetrahydrofurans 7 and 19, piperidines 13, 15 and 21, and pyrrolidines 17 and 18. (C) 1997, Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(96)02403-3
• 作为产物：
  描述：

  二碳酸二叔丁酯 在 碳酸氢钠 作用下， 以 二甲基亚砜 为溶剂， 生成 (2R,3R,4R,5S)-2-(tert-Butoxycarbonylamino-methyl)-5-cyanomethyl-3,4-dihydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Intramolecular cyclization of C2 symmetric and meso-iodo amino alcohols: A synthetic approach to azasugars

  摘要：

  C-2 Symmetric and meso-iodo hydroxy ammonium chlorides generated from 2 and 5 have been cyclized under basic conditions to produce various heterocycles chemoselectively, which comprise tetrahydrofurans 7 and 19, piperidines 13, 15 and 21, and pyrrolidines 17 and 18. (C) 1997, Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(96)02403-3