1,2;3,4:5,6-tri-O-isopropylidene-D-glucitol

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,2;3,4:5,6-tri-O-isopropylidene-D-glucitol
• 英文别名: D-glucitol 1,2;3,4;5,6-tris(acetonide)；(4S,5S)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-4-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-1,3-dioxolane
• 化学式: C₁₅H₂₆O₆
• 分子量: 302.368
• InChiKey: CKECEWYVEGPMPE-USZNOCQGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  55.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1,2;3,4:5,6-tri-O-isopropylidene-D-glucitol 在 溶剂黄146 作用下， 以 水 为溶剂， 反应 0.58h， 以71%的产率得到D-glucitol 3,4-acetonide
  参考文献：
  名称：

  Polymer-mediated cyclodehydration of alditols and ketohexoses

  摘要：

  The polymer PEDOT+ (1 or 2) mediates a cyclodehydration reaction with alditols 3, 5, 7, 9, in hydrocarbon solvents, to give cyclic ethers 4, 6, 8, or 10, respectively, in high yield with a trivial isolation protocol. Polymers 1 or 2 also mediate the cyclodehydration of ketohexoses such as D-fructose, but not aldohexoses, to the important industrial intermediate 5-hydroxymethylfurfural (17), under milder conditions when compared to reactions mediated by mineral acids. A cascade reaction with ketohexoses is observed in toluene via cyclodehydration followed by Friedel-Crafts alkylation of the initially formed benzylic alcohol to give 16. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2011.04.017
• 作为产物：
  描述：

  山梨醇 、 丙酮 在 硫酸 作用下， 反应 18.0h， 以67%的产率得到1,2;3,4:5,6-tri-O-isopropylidene-D-glucitol
  参考文献：
  名称：

  Polymer-mediated cyclodehydration of alditols and ketohexoses

  摘要：

  The polymer PEDOT+ (1 or 2) mediates a cyclodehydration reaction with alditols 3, 5, 7, 9, in hydrocarbon solvents, to give cyclic ethers 4, 6, 8, or 10, respectively, in high yield with a trivial isolation protocol. Polymers 1 or 2 also mediate the cyclodehydration of ketohexoses such as D-fructose, but not aldohexoses, to the important industrial intermediate 5-hydroxymethylfurfural (17), under milder conditions when compared to reactions mediated by mineral acids. A cascade reaction with ketohexoses is observed in toluene via cyclodehydration followed by Friedel-Crafts alkylation of the initially formed benzylic alcohol to give 16. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2011.04.017

文献信息

• A Simple and Clean Method for O-Isopropylidenation of Carbohydrates
  作者：Yuan Wei Rong、Qi Hua Zhang、Wei Wang、Bao Lin Li

  DOI：10.5012/bkcs.2014.35.7.2165

  日期：2014.7.20
• Polymer-mediated cyclodehydration of alditols and ketohexoses
  作者：Amber Onorato、Christopher Pavlik、Michael A. Invernale、Ian D. Berghorn、Gregory A. Sotzing、Martha D. Morton、Michael B. Smith

  DOI：10.1016/j.carres.2011.04.017

  日期：2011.9

  The polymer PEDOT+ (1 or 2) mediates a cyclodehydration reaction with alditols 3, 5, 7, 9, in hydrocarbon solvents, to give cyclic ethers 4, 6, 8, or 10, respectively, in high yield with a trivial isolation protocol. Polymers 1 or 2 also mediate the cyclodehydration of ketohexoses such as D-fructose, but not aldohexoses, to the important industrial intermediate 5-hydroxymethylfurfural (17), under milder conditions when compared to reactions mediated by mineral acids. A cascade reaction with ketohexoses is observed in toluene via cyclodehydration followed by Friedel-Crafts alkylation of the initially formed benzylic alcohol to give 16. (C) 2011 Elsevier Ltd. All rights reserved.