6-bromo-6-deoxy-D-mannitol | 15430-94-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-bromo-6-deoxy-D-mannitol
• 英文别名: 1-bromo-D-1-deoxy-mannitol；6-Brom-6-desoxy-D-mannitol；6-Bromohexane-1,2,3,4,5-pentol；(2R,3R,4S,5S)-6-bromohexane-1,2,3,4,5-pentol
• CAS: 15430-94-1
• 化学式: C₆H₁₃BrO₅
• 分子量: 245.07
• InChiKey: IBXOWOYVOOTHAW-KVTDHHQDSA-N

物化性质

• 沸点：
  543.9±50.0 °C(Predicted)
• 密度：
  1.888±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.7
• 重原子数：
  12
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  101
• 氢给体数：
  5
• 氢受体数：
  5

安全信息

• 海关编码：
  2905590090

反应信息

• 作为反应物：
  描述：

  6-bromo-6-deoxy-D-mannitol 以 水 为溶剂， 反应 3.0h， 以68%的产率得到1,4-脱水己糖醇
  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
• 作为产物：
  描述：

  D-甘露糖-1,4-内酯 在 sodium tetrahydroborate 、 高氯酸 、 四溴化碳 、 ion exchange resin (IR-120 、 氢气 、 乙酰氯 、 三苯基膦 作用下， 反应 4.0h， 生成 6-bromo-6-deoxy-D-mannitol
  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

文献信息

• Institoris; Horvath; Csanyi, Arzneimittel-Forschung/Drug Research, 1967, vol. 17, # 2, p. 145 - 149
  作者：Institoris、Horvath、Csanyi

  DOI：——

  日期：——
• Enantiomerically pure, highly functionalized tetrahydrofurans from simple carbohydrate precursors
  作者：Inge Lundt、Holger Frank

  DOI：10.1016/s0040-4020(01)89337-6

  日期：1994.1

  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.