ethyl 2-((2R,3R,4S,5R,6R)-2-azido-4,5-bis(benzyloxy)-6-methyl-tetrahydro-2H-pyran-3-yloxy)acetate | 1314093-62-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: ethyl 2-((2R,3R,4S,5R,6R)-2-azido-4,5-bis(benzyloxy)-6-methyl-tetrahydro-2H-pyran-3-yloxy)acetate
• 英文别名: ethyl 2-[(2R,3R,4S,5R,6R)-2-azido-6-methyl-4,5-bis(phenylmethoxy)oxan-3-yl]oxyacetate
• CAS: 1314093-62-3
• 化学式: C₂₄H₂₉N₃O₆
• 分子量: 455.511
• InChiKey: GZCGHICUPCHMNF-ASDZUOGYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  33
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  77.6
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  ethyl 2-((2R,3R,4S,5R,6R)-2-azido-4,5-bis(benzyloxy)-6-methyl-tetrahydro-2H-pyran-3-yloxy)acetate 在 20 % Pd(OH)2/C 、 氢气 作用下， 以 乙醇 为溶剂， 20.0 ℃ 、506.66 kPa 条件下， 以86%的产率得到(4aR,6R,7S,8S,8aR)-7,8-dihydroxy-6-methylhexahydropyrano[3,2-b][1,4]oxazin-3(2H)-one
  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-3,4-di-O-benzyl-6-desoxy-D-glucopyranose 在 sodium azide 、 ammonium cerium (IV) nitrate 、 水 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 、 paraffin oil 为溶剂， 反应 1.08h， 生成 ethyl 2-((2R,3R,4S,5R,6R)-2-azido-4,5-bis(benzyloxy)-6-methyl-tetrahydro-2H-pyran-3-yloxy)acetate
  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.