3,6-anhydro-1,2-4,5-di-O-isopropyliden-D-altritol | 106624-64-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,6-anhydro-1,2-4,5-di-O-isopropyliden-D-altritol
• 英文别名: 1,4-Anhydro-2,3:5,6-di-O-isopropyliden-D-talit；3,6-Anhydro-1,2:4,5-di-O-isopropyliden-D-altrit
• CAS: 106624-64-0
• 化学式: C₁₂H₂₀O₅
• 分子量: 244.288
• InChiKey: ODFSPVXJTALZSK-DOLQZWNJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.06
• 重原子数：
  17.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  46.15
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  6-bromo-6-deoxy-D-altrono-1,4-lactone 在 sodium tetrahydroborate 、 乙酰氯 作用下， 以 甲醇 、 乙醇 、 水 为溶剂， 反应 4.0h， 生成 3,6-anhydro-1,2-4,5-di-O-isopropyliden-D-altritol
  参考文献：
  名称：

  Enantiomerically pure, highly functionalized tetrahydrofurans from simple carbohydrate precursors

  摘要：

  6-Bromo-6-deoxy-1,4-aldonolactones and 6-bromo-6-deoxy-alditols with D-galacto-, D-altro-, D-manno- and D-ido-configuration were selectively converted into hydroxylated tetrahydrofuran derivatives by simple heating in water. The 6-bromo-6-deoxy-D-altritol (10) and 6-bromo-6-deoxy-D-iditol (25) reacted even at room temperature. Likewise, the 6-bromo-2,6-dideoxy-aldonolactones with D-arabino- (29) and D-lyxo-configuration (31) gave the corresponding 2-deoxy-3,6-anhydrides, when heated in water. The rate of formation of the furan ring by intramolecular nucleophilic substitution was determined by the conformation of the bromopolyols in water.

  DOI：

  10.1016/s0040-4020(01)89337-6