(5aR,6S,7S,8R,9aR)-8-hydroxymethyl-4,5a,6,7,8,9a-hexahydropyrano[3,2-b][1,2,3]triazolo[1,5-d][1,4]oxazine-6,7-diol | 1314093-41-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (5aR,6S,7S,8R,9aR)-8-hydroxymethyl-4,5a,6,7,8,9a-hexahydropyrano[3,2-b][1,2,3]triazolo[1,5-d][1,4]oxazine-6,7-diol
• 英文别名: (1R,9R,10S,11S,12R)-12-(hydroxymethyl)-8,13-dioxa-2,3,4-triazatricyclo[7.4.0.02,6]trideca-3,5-diene-10,11-diol
• CAS: 1314093-41-8
• 化学式: C₉H₁₃N₃O₅
• 分子量: 243.219
• InChiKey: WRSFWVDIZNUIKS-SYHAXYEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.4
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  110
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (5aR,6S,7S,8R,9aR)-8-hydroxymethyl-4,5a,6,7,8,9a-hexahydropyrano[3,2-b][1,2,3]triazolo[1,5-d][1,4]oxazine-6,7-diol 、 乙酸酐 在 吡啶 作用下， 以88%的产率得到(5aR,6S,7R,8R,9aR)-8-acetoxymethyl-4,5a,6,7,8,9a-hexahydropyrano[3,2-b][1,2,3]triazolo[1,5-d][1,4]oxazine-6,7-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
• 作为产物：
  描述：

  3,4,6-tri-O-benzyl-β-D-glucopyranosyl azide 在 20 % Pd(OH)2/C 、 水 、 氢气 、 sodium hydride 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 70.0 ℃ 、506.66 kPa 条件下， 反应 0.08h， 生成 (5aR,6S,7S,8R,9aR)-8-hydroxymethyl-4,5a,6,7,8,9a-hexahydropyrano[3,2-b][1,2,3]triazolo[1,5-d][1,4]oxazine-6,7-diol
  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

文献信息

• 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
  作者：Y. Suman Reddy、A. P. John Pal、Preeti Gupta、Alafia A. Ansari、Yashwant D. Vankar

  DOI：10.1021/jo200260w

  日期：2011.8.5

  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.