((5R,6R,7R,7aS)-6,7-Dihydroxy-3-oxo-tetrahydro-pyrrolo[1,2-c]oxazol-5-ylmethyl)-carbamic acid tert-butyl ester | 188019-27-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: ((5R,6R,7R,7aS)-6,7-Dihydroxy-3-oxo-tetrahydro-pyrrolo[1,2-c]oxazol-5-ylmethyl)-carbamic acid tert-butyl ester
• 英文别名: tert-butyl N-[[(5R,6R,7R,7aS)-6,7-dihydroxy-3-oxo-5,6,7,7a-tetrahydro-1H-pyrrolo[1,2-c][1,3]oxazol-5-yl]methyl]carbamate
• CAS: 188019-27-4
• 化学式: C₁₂H₂₀N₂O₆
• 分子量: 288.301
• InChiKey: ZVQFJMRAGBLEGR-BZNPZCIMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.83
• 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：

  ((5R,6R,7R,7aS)-6,7-Dihydroxy-3-oxo-tetrahydro-pyrrolo[1,2-c]oxazol-5-ylmethyl)-carbamic acid tert-butyl ester 在 barium dihydroxide 作用下， 以 水 为溶剂， 生成 1-amino-1,2,5-trideoxy-2,5-imino-D-glucitol
  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：

  (2S,2'S)-<(1R,2R)-1,2-dibenzyloxy-ethan-diyl>bis(1-tert-butoxycarbonyl)-aziridine 在 钯 dilithium tetrabromonickelate(II) 、 氢气 作用下， 以 四氢呋喃 、 溶剂黄146 为溶剂， 70.0 ℃ 、101.33 kPa 条件下， 反应 9.0h， 生成 ((5R,6R,7R,7aS)-6,7-Dihydroxy-3-oxo-tetrahydro-pyrrolo[1,2-c]oxazol-5-ylmethyl)-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Synthesis and evaluation as glycosidase inhibitors of 2,5-imino- d -glucitol and 1,5-imino- d -mannitol related derivatives

  摘要：

  Selectively functionalized 2,5-imino-D-glucitol and 1,5-imino-D-mannitol derivatives were synthesized and tested as precursors of hydrolytically resistant pseudo-disaccharides. Among them N-acetyl-6-amino-6-deoxy-2,5-imino-D-glucitol (11) and N-acetyl-6-amino-6-deoxy- 1,5-imino-D-mannitol (12) were found potent and specific inhibitors against beta-D-glucosidase and alpha-L-fucosidase, respectively. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(99)00267-9

文献信息

• Intramolecular cyclization of C2 symmetric and meso-iodo amino alcohols: A synthetic approach to azasugars
  作者：Sung Ho Kang、Do Hyun Ryu

  DOI：10.1016/s0040-4039(96)02403-3

  日期：1997.1

  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.
• Synthesis and evaluation as glycosidase inhibitors of 2,5-imino- d -glucitol and 1,5-imino- d -mannitol related derivatives
  作者：Isabelle McCort、Sébastien Fort、Annie Duréault、Jean-Claude Depezay

  DOI：10.1016/s0968-0896(99)00267-9

  日期：2000.1

  Selectively functionalized 2,5-imino-D-glucitol and 1,5-imino-D-mannitol derivatives were synthesized and tested as precursors of hydrolytically resistant pseudo-disaccharides. Among them N-acetyl-6-amino-6-deoxy-2,5-imino-D-glucitol (11) and N-acetyl-6-amino-6-deoxy- 1,5-imino-D-mannitol (12) were found potent and specific inhibitors against beta-D-glucosidase and alpha-L-fucosidase, respectively. (C) 2000 Elsevier Science Ltd. All rights reserved.