(1S)-1,2:3,4:5,6-tri-O-isopropylidene-1-methoxy-D-glucitol | 35988-31-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1S)-1,2:3,4:5,6-tri-O-isopropylidene-1-methoxy-D-glucitol
• 英文别名: (4R,5S)-4-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-5-[(4R,5S)-5-methoxy-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-1,3-dioxolane
• CAS: 35988-31-9
• 化学式: C₁₆H₂₈O₇
• 分子量: 332.394
• InChiKey: AAXKVQFOTQWFCJ-LBELIVKGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  64.6
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  乙酸酐 、 2,2-二甲氧基丙烷 、 蔗糖 在 对甲苯磺酸 、 吡啶 作用下， 以 1,4-二氧六环 为溶剂， 反应 14.0h， 以68%的产率得到methyl 4,6-di-O-acetyl-1,3-O-isopropylidene-α-D-fructofuranoside
  参考文献：
  名称：

  An efficient synthesis of methyl 1,3-O-isopropylidene-α-d-fructofuranoside and 2,3:5,6-di-O-isopropylidene-d-glucose dimethyl acetal derivatives from sucrose

  摘要：

  Acetalation of sucrose with 2,2-dimethoxypropane in 1,4-dioxane in the presence of p-toluenesulfonic acid, followed by acetylation, afforded methyl 4,6-di-O-acetyl-1,3-O-isopropylidene-alpha-D-fructofuranoside and 4-O-acetyl-2,3:5,6-di-O-isopropylidene-D-glucose dimethyl acetal as major products, while tosylation of the intermediate acetals provided methyl 6-O-tosyl-1,3-O-isopropytidene-alpha-D-fructofuranose. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2005.07.023

文献信息

• An efficient synthesis of methyl 1,3-O-isopropylidene-α-d-fructofuranoside and 2,3:5,6-di-O-isopropylidene-d-glucose dimethyl acetal derivatives from sucrose
  作者：Tadashi Hanaya、Nobuaki Sato、Hiroshi Yamamoto

  DOI：10.1016/j.carres.2005.07.023

  日期：2005.11

  Acetalation of sucrose with 2,2-dimethoxypropane in 1,4-dioxane in the presence of p-toluenesulfonic acid, followed by acetylation, afforded methyl 4,6-di-O-acetyl-1,3-O-isopropylidene-alpha-D-fructofuranoside and 4-O-acetyl-2,3:5,6-di-O-isopropylidene-D-glucose dimethyl acetal as major products, while tosylation of the intermediate acetals provided methyl 6-O-tosyl-1,3-O-isopropytidene-alpha-D-fructofuranose. (C) 2005 Elsevier Ltd. All rights reserved.