(2R,3S,4S)-4-azido-2-dimethoxymethyl-3-benzyloxytetrahydrofuran | 1362047-66-2

• 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,3S,4S)-4-azido-2-dimethoxymethyl-3-benzyloxytetrahydrofuran
• CAS: 1362047-66-2
• 化学式: C₁₄H₁₉N₃O₄
• 分子量: 293.323
• InChiKey: IBWHDBAAQPVCTJ-RWMBFGLXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.27
• 重原子数：
  21.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  85.68
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (2R,3S,4S)-4-azido-2-dimethoxymethyl-3-benzyloxytetrahydrofuran 在 盐酸 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 3.0h， 以90.8%的产率得到2,5-anhydro-4-azido-3-O-benzyl-4-deoxy-L-arabinose
  参考文献：
  名称：

  An efficient and convenient formal synthesis of Jaspine B from d-xylose

  摘要：

  A formal synthesis of Jaspine B was completed in 42.4% overall yield with only three purification steps (one by crystallization and two by column chromatography). The key step in the synthesis involves a regio- and stereoselective epoxide ring-opening reaction and the configuration inversion of the C3-hydroxyl group through oxidation and reduction. All of the reagents and materials used were quite common and inexpensive. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2012.01.013
• 作为产物：
  描述：

  2,2-dimethyl-6-(4-methylphenylsulfonyloxymethyl)-5-(4-methylphenylsulfonyloxymethyl)-(3aR,5R,6S,6aR)-perhydrofuro[2,3-d][1,3]dioxole 在 sodium azide 、 钾硼氢 、 potassium carbonate 、 氯化铵 、 乙酰氯 、 2-碘酰基苯甲酸 作用下， 以 四氢呋喃 、 乙醇 、 水 、 乙酸乙酯 为溶剂， 反应 64.0h， 生成 (2R,3S,4S)-4-azido-2-dimethoxymethyl-3-benzyloxytetrahydrofuran
  参考文献：
  名称：

  An efficient and convenient formal synthesis of Jaspine B from d-xylose

  摘要：

  A formal synthesis of Jaspine B was completed in 42.4% overall yield with only three purification steps (one by crystallization and two by column chromatography). The key step in the synthesis involves a regio- and stereoselective epoxide ring-opening reaction and the configuration inversion of the C3-hydroxyl group through oxidation and reduction. All of the reagents and materials used were quite common and inexpensive. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2012.01.013