(2R,3R,4R,5R,6R)-2-azido-4,5-bis(4-methoxybenzyloxy)-6-((4-methoxybenzyloxy)methyl)tetrahydro-2H-pyran-3-ol | 1314093-22-5

• 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: (2R,3R,4R,5R,6R)-2-azido-4,5-bis(4-methoxybenzyloxy)-6-((4-methoxybenzyloxy)methyl)tetrahydro-2H-pyran-3-ol
• 英文别名: Mob(-3)[Mob(-4)][Mob(-6)]Glc(b)-N3；(2R,3R,4R,5R,6R)-2-azido-4,5-bis[(4-methoxyphenyl)methoxy]-6-[(4-methoxyphenyl)methoxymethyl]oxan-3-ol
• CAS: 1314093-22-5
• 化学式: C₃₀H₃₅N₃O₈
• 分子量: 565.623
• InChiKey: IMUZBBUJRGFICI-XZTOTZIXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  41
• 可旋转键数：
  14
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  99.2
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  (1S,3R,4R,5S,6R)-4,5-bis((4-methoxybenzyl)oxy)-3-(((4-methoxybenzyl)oxy)methyl)-2,7-dioxabicyclo[4.1.0]heptane 在 sodium azide 、 ammonium cerium (IV) nitrate 、 水 作用下， 以 乙腈 为溶剂， 反应 0.08h， 以83%的产率得到(2R,3R,4R,5R,6R)-2-azido-4,5-bis(4-methoxybenzyloxy)-6-((4-methoxybenzyloxy)methyl)tetrahydro-2H-pyran-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.