Acetic acid (1R,2S,3S,4S,5S)-2,3-diacetoxy-5-methyl-7-oxo-8-oxa-6-aza-bicyclo[3.2.1]oct-4-yl ester | 223527-77-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧杂环己烷
• 英文名称: Acetic acid (1R,2S,3S,4S,5S)-2,3-diacetoxy-5-methyl-7-oxo-8-oxa-6-aza-bicyclo[3.2.1]oct-4-yl ester
• 英文别名: [(1R,2S,3S,4S,5S)-3,4-diacetyloxy-5-methyl-7-oxo-8-oxa-6-azabicyclo[3.2.1]octan-2-yl] acetate
• CAS: 223527-77-3
• 化学式: C₁₃H₁₇NO₈
• 分子量: 315.28
• InChiKey: DDYBJKQVYTXIGX-JPYZYGQNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  117
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  Acetic acid (1R,2S,3S,4S,5S)-2,3-diacetoxy-5-methyl-7-oxo-8-oxa-6-aza-bicyclo[3.2.1]oct-4-yl ester 在 sodium methylate 作用下， 以 甲醇 为溶剂， 生成 (1R,2S,3S,4S,5S)-2,3,4-Trihydroxy-5-methyl-8-oxa-6-aza-bicyclo[3.2.1]octan-7-one
  参考文献：
  名称：

  Components for a combinatorial library of rigid azabicyclic α-L-fucose mimics: First X-ray crystal structure of a stable monoalkylated triazene formed by hydrogenation of an azide

  摘要：

  Photobromination of the rigid aza-bicyclic fucose mimic 3 gave a reactive glycosyl type bromide 7 as a divergent intermediate for the synthesis of both 7-O and 7-N linked bicyclic L-fucose derivatives by direct displacement with alcohols or amines. Displacement of the bromide 7 with sodium azide gave an azide 6 which on hydrogenation gave a stable monoalkyl triazene 5 the structure of which was established by X-ray crystallographic analysis. Hydrolysis of 7 allowed access to a monocyclic L-fucose mimic with a nitrogen substituent at C-5. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)00378-0
• 作为产物：
  描述：

  [(1S,2R,3S,4S,5S)-6-acetyl-3,4-diacetyloxy-5-methyl-8-oxa-6-azabicyclo[3.2.1]octan-2-yl] acetate 在 molecular sieve 、 溴 、 pyridinium chlorochromate 、 甲胺 作用下， 以 二氯甲烷 、 三氯乙烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 Acetic acid (1R,2S,3S,4S,5S)-2,3-diacetoxy-5-methyl-7-oxo-8-oxa-6-aza-bicyclo[3.2.1]oct-4-yl ester
  参考文献：
  名称：

  Components for a combinatorial library of rigid azabicyclic α-L-fucose mimics: First X-ray crystal structure of a stable monoalkylated triazene formed by hydrogenation of an azide

  摘要：

  Photobromination of the rigid aza-bicyclic fucose mimic 3 gave a reactive glycosyl type bromide 7 as a divergent intermediate for the synthesis of both 7-O and 7-N linked bicyclic L-fucose derivatives by direct displacement with alcohols or amines. Displacement of the bromide 7 with sodium azide gave an azide 6 which on hydrogenation gave a stable monoalkyl triazene 5 the structure of which was established by X-ray crystallographic analysis. Hydrolysis of 7 allowed access to a monocyclic L-fucose mimic with a nitrogen substituent at C-5. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)00378-0