(2R,3R,4R,5R)-2-(tert-Butoxycarbonylamino-methyl)-3,4-dihydroxy-5-iodomethyl-pyrrolidine-1-carboxylic acid tert-butyl ester | 188019-26-3

• 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,5R)-2-(tert-Butoxycarbonylamino-methyl)-3,4-dihydroxy-5-iodomethyl-pyrrolidine-1-carboxylic acid tert-butyl ester
• 英文别名: tert-butyl (2R,3R,4R,5R)-3,4-dihydroxy-2-(iodomethyl)-5-[[(2-methylpropan-2-yl)oxycarbonylamino]methyl]pyrrolidine-1-carboxylate
• CAS: 188019-26-3
• 化学式: C₁₆H₂₉IN₂O₆
• 分子量: 472.321
• InChiKey: KKACQYPGIFRDGY-IRCOFANPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  108
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2R,3R,4R,5R)-2-(tert-Butoxycarbonylamino-methyl)-3,4-dihydroxy-5-iodomethyl-pyrrolidine-1-carboxylic acid tert-butyl ester 在 barium dihydroxide 、 sodium hydroxide 、 silver(I) acetate 作用下， 以 水 、 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， 生成 N-[[(2R,3R,4R,5S)-3,4-dihydroxy-5-(hydroxymethyl)pyrrolidin-2-yl]methyl]acetamide
  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：

  (4R,4aR,8R,8aR)-4,8-Bis-iodomethyl-2,6-bis-trichloromethyl-4,4a,8,8a-tetrahydro-1,5-dioxa-3,7-diaza-naphthalene 在 盐酸 、 methyloxirane 作用下， 以 甲醇 为溶剂， 生成 (2R,3R,4R,5R)-2-(tert-Butoxycarbonylamino-methyl)-3,4-dihydroxy-5-iodomethyl-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