(2S,3R,4R,5R)-2-azido-4-benzyloxy-5-(benzyloxymethyl)tetrahydrofuran-3-ol | 1314093-27-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3R,4R,5R)-2-azido-4-benzyloxy-5-(benzyloxymethyl)tetrahydrofuran-3-ol
• 英文别名: (2S,3S,4R,5R)-2-azido-4-phenylmethoxy-5-(phenylmethoxymethyl)oxolan-3-ol
• CAS: 1314093-27-0
• 化学式: C₁₉H₂₁N₃O₄
• 分子量: 355.393
• InChiKey: GAGZILMVDGAWIB-XWSJACJDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  62.3
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2S,3R,4R,5R)-2-azido-4-benzyloxy-5-(benzyloxymethyl)tetrahydrofuran-3-ol 在 水 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.08h， 生成 (5aS,6S,7R,8aS)-6-benzyloxy-7-(benzyloxymethyl)-5a,6,7,8a-tetrahydro-4H-furo[3,2-b][1,2,3]triazolo[1,5-d][1,4]oxazine
  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：

  1,2-Anhydro-3,5-di-O-benzyl-β-D-lyxofuranose 在 sodium azide 、 ammonium cerium (IV) nitrate 、 水 作用下， 以 乙腈 为溶剂， 反应 0.08h， 以64%的产率得到(2S,3R,4R,5R)-2-azido-4-benzyloxy-5-(benzyloxymethyl)tetrahydrofuran-3-ol
  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.