methyl 1,3-O-isopropylidene-4,6-di-O-tosyl-α-D-fructofuranoside

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl 1,3-O-isopropylidene-4,6-di-O-tosyl-α-D-fructofuranoside
• 英文别名: [(4aS,6R,7R,7aS)-4a-methoxy-2,2-dimethyl-7-(4-methylphenyl)sulfonyloxy-4,6,7,7a-tetrahydrofuro[3,2-d][1,3]dioxin-6-yl]methyl 4-methylbenzenesulfonate
• 化学式: C₂₄H₃₀O₁₀S₂
• 分子量: 542.628
• InChiKey: NTPYWCDPSSHURE-SVPADUAOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  36
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  140
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  methyl 4,6-di-O-acetyl-1,3-O-isopropylidene-α-D-fructofuranoside 在 吡啶 、 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 13.0h， 生成 methyl 1,3-O-isopropylidene-4,6-di-O-tosyl-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.