[(1S,2R,3S,4S,5S,7S)-6-acetyl-3,4-diacetyloxy-7-(aminodiazenyl)-5-methyl-8-oxa-6-azabicyclo[3.2.1]octan-2-yl] acetate | 223537-67-5

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: [(1S,2R,3S,4S,5S,7S)-6-acetyl-3,4-diacetyloxy-7-(aminodiazenyl)-5-methyl-8-oxa-6-azabicyclo[3.2.1]octan-2-yl] acetate
• CAS: 223537-67-5
• 化学式: C₁₅H₂₂N₄O₈
• 分子量: 386.362
• InChiKey: DVHWYYQKVQTWFU-UJOWSUJOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  159
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  [(1S,2R,3S,4S,5S,7S)-6-acetyl-3,4-diacetyloxy-7-(aminodiazenyl)-5-methyl-8-oxa-6-azabicyclo[3.2.1]octan-2-yl] acetate 在 溴 作用下， 以 甲醇 为溶剂， 以60%的产率得到Acetic acid (1S,2R,3S,4S,5S,7S)-2,3-diacetoxy-6-acetyl-7-azido-5-methyl-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
• 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 钯 sodium azide 、 氢气 、 溴 作用下， 以 三氯乙烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 [(1S,2R,3S,4S,5S,7S)-6-acetyl-3,4-diacetyloxy-7-(aminodiazenyl)-5-methyl-8-oxa-6-azabicyclo[3.2.1]octan-2-yl] acetate
  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