(4aR,7S,8S,8aR)-4-acetyl-3-oxo-octahydropyrano[3,2-b][1,4]oxazine-7,8-diyl diacetate | 1314093-76-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4aR,7S,8S,8aR)-4-acetyl-3-oxo-octahydropyrano[3,2-b][1,4]oxazine-7,8-diyl diacetate
• 英文别名: [(4aR,7S,8S,8aR)-4-acetyl-8-acetyloxy-3-oxo-6,7,8,8a-tetrahydro-4aH-pyrano[3,2-b][1,4]oxazin-7-yl] acetate
• CAS: 1314093-76-9
• 化学式: C₁₃H₁₇NO₈
• 分子量: 315.28
• InChiKey: OQIJVMABXSZHMC-FTYKPCCVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  108
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  ethyl 2-((2R,3R,4S,5S)-2-azido-4,5-bis(benzyloxy)-tetrahydro-2H-pyran-3-yloxy)acetate 在 吡啶 、 20 % Pd(OH)2/C 、 氢气 作用下， 以 乙醇 为溶剂， 20.0 ℃ 、506.66 kPa 条件下， 反应 10.0h， 生成 (4aR,7S,8S,8aR)-4-acetyl-3-oxo-octahydropyrano[3,2-b][1,4]oxazine-7,8-diyl diacetate
  参考文献：
  名称：

  Ceric Ammonium Nitrate-Catalyzed Azidation of 1,2-Anhydro Sugars: Application in the Synthesis of Structurally Diverse Sugar-Derived Morpholine 1,2,3-Triazoles and 1,4-Oxazin-2-ones

  摘要：

  Azidation of 1,2-anhydro sugars with NaN3 in CH3CN by using a catalytic amount of ceric ammonium nitrate has been accomplished in a regio- and stereoselective manner. Various 1,2-anhydro sugars produced 2-hydroxy-1-azido sugars in good yields which, in turn, were converted to structurally diverse sugar-derived morpholine triazoles and sugar oxazin-2-ones. These sugar derivatives were tested against various commercially available glycosidases, and two of them were found to be active in the micromolar range.

  DOI：

  10.1021/jo200260w