1,2-O-isopropylidene-α-L-fructopyranose | 161754-12-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,2-O-isopropylidene-α-L-fructopyranose
• 英文别名: (5S,6R,7S,8S)-2,2-dimethyl-1,3,10-trioxaspiro[4.5]decane-6,7,8-triol
• CAS: 161754-12-7
• 化学式: C₉H₁₆O₆
• 分子量: 220.222
• InChiKey: NCPKAWHTYZABFG-LKHWLPBLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.8
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  88.4
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1,2-O-isopropylidene-α-L-fructopyranose 在 硫酸 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以67%的产率得到L-Fructose
  参考文献：
  名称：

  Application of a phase transfer reaction to the synthesis of l-fructose

  摘要：

  L-Fructose was prepared in five steps from L-sorbose (1). 1,2-O-Isopropylidene-alpha-L-sorbopyranose (2), prepared from 1, was selectively tosylated using phase transfer catalysis to give 1,2-O-isopropylidene-3-O- (p-tolylsulfonyl)-alpha-L-sorbopyranose (3). Formation of a 3,4-anhydro ring, followed by its base-catalyzed opening to effect overall inversion of configuration at both C-3 and C-4 gave 1,2-O-isopropylidene-alpha-L-fructopyranose (5), which was deacetonated to yield L-fructose (6).

  DOI：

  10.1016/0008-6215(94)00255-e
• 作为产物：
  描述：

  L-sorbopyranose 在 sodium hydroxide 、 四丁基硫酸氢铵 、 copper(II) sulfate 作用下， 以 甲醇 、 二氯甲烷 、 丙酮 为溶剂， 反应 59.42h， 生成 1,2-O-isopropylidene-α-L-fructopyranose
  参考文献：
  名称：

  Application of a phase transfer reaction to the synthesis of l-fructose

  摘要：

  L-Fructose was prepared in five steps from L-sorbose (1). 1,2-O-Isopropylidene-alpha-L-sorbopyranose (2), prepared from 1, was selectively tosylated using phase transfer catalysis to give 1,2-O-isopropylidene-3-O- (p-tolylsulfonyl)-alpha-L-sorbopyranose (3). Formation of a 3,4-anhydro ring, followed by its base-catalyzed opening to effect overall inversion of configuration at both C-3 and C-4 gave 1,2-O-isopropylidene-alpha-L-fructopyranose (5), which was deacetonated to yield L-fructose (6).

  DOI：

  10.1016/0008-6215(94)00255-e

文献信息

• Application of a phase transfer reaction to the synthesis of l-fructose
  作者：Yonas Gizaw、James N. BeMiller

  DOI：10.1016/0008-6215(94)00255-e

  日期：1995.1

  L-Fructose was prepared in five steps from L-sorbose (1). 1,2-O-Isopropylidene-alpha-L-sorbopyranose (2), prepared from 1, was selectively tosylated using phase transfer catalysis to give 1,2-O-isopropylidene-3-O- (p-tolylsulfonyl)-alpha-L-sorbopyranose (3). Formation of a 3,4-anhydro ring, followed by its base-catalyzed opening to effect overall inversion of configuration at both C-3 and C-4 gave 1,2-O-isopropylidene-alpha-L-fructopyranose (5), which was deacetonated to yield L-fructose (6).