1,2-O-cyclohexylidene-3,5,6-O-trivinyl-α-D-glucofuranose

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,2-O-cyclohexylidene-3,5,6-O-trivinyl-α-D-glucofuranose
• 英文别名: (3aR,5R,6S,6aR)-5-[(1R)-1,2-bis(ethenoxy)ethyl]-6-ethenoxyspiro[3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxole-2,1'-cyclohexane]
• 化学式: C₁₈H₂₆O₆
• 分子量: 338.401
• InChiKey: HBLYDMLIRSWUJL-NQNKBUKLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  55.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  1,2-O-亚环己基-Alpha-D-呋喃葡萄糖 、 乙炔 在 potassium tert-butylate 作用下， 以 二甲基亚砜 为溶剂， 113.0~117.0 ℃ 、101.33 kPa 条件下， 反应 15.0h， 以79%的产率得到1,2-O-cyclohexylidene-3,5,6-O-trivinyl-α-D-glucofuranose
  参考文献：
  名称：

  Direct vinylation of glucose derivatives with acetylene

  摘要：

  Vinyl ethers, promising chiral carbohydrate synthons, have been synthesized by the addition of glucose acetals (1,2: 5,6-di-O-isopropylidene-alpha-D-glucofuranose, methyl 4,6-O-benzylidene-alpha-D-glucopyranoside, 1,2-O-cyclohexylidene-alpha-D-glucofuranose, methyl alpha-D-glucopyranoside) to acetylene under atmospheric and elevated pressures in an autoclave in the presence of superbase catalytic systems (KOH-DMSO, t-BuOK-DMSO). The complete vinylation of 1,2: 5,6-di-O-isopropylidene-alpha-D-glucofuranose and methyl alpha-D-glucopyranoside has been realized under elevated pressure of acetylene in the system KOH-THF as well. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.08.107

文献信息

• Direct vinylation of glucose derivatives with acetylene
  作者：Boris A. Trofimov、Lidiya N. Parshina、Ludmila A. Oparina、Anatolii P. Tantsyrev、Marina Ya. Khil'ko、Oksana V. Vysotskaya、Andrey V. Stepanov、Nina K. Gusarova、Jochem Henkelmann

  DOI：10.1016/j.tet.2007.08.107

  日期：2007.11

  Vinyl ethers, promising chiral carbohydrate synthons, have been synthesized by the addition of glucose acetals (1,2: 5,6-di-O-isopropylidene-alpha-D-glucofuranose, methyl 4,6-O-benzylidene-alpha-D-glucopyranoside, 1,2-O-cyclohexylidene-alpha-D-glucofuranose, methyl alpha-D-glucopyranoside) to acetylene under atmospheric and elevated pressures in an autoclave in the presence of superbase catalytic systems (KOH-DMSO, t-BuOK-DMSO). The complete vinylation of 1,2: 5,6-di-O-isopropylidene-alpha-D-glucofuranose and methyl alpha-D-glucopyranoside has been realized under elevated pressure of acetylene in the system KOH-THF as well. (c) 2007 Elsevier Ltd. All rights reserved.