2,3,4,6-tetra(O-vinyl) methyl α-D-glucopyranoside | 68091-35-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3,4,6-tetra(O-vinyl) methyl α-D-glucopyranoside
• 英文别名: methyl 2,3,4,6-O-tetravinyl-α-D-glucopyranoside；methyl-(tetra-O-vinyl-α-D-glucopyranoside)；Methyl-(tetra-O-vinyl-α-D-glucopyranosid)；(2R,3R,4S,5R,6S)-3,4,5-tris(ethenoxy)-2-(ethenoxymethyl)-6-methoxyoxane
• CAS: 68091-35-0
• 化学式: C₁₅H₂₂O₆
• 分子量: 298.336
• InChiKey: GOCJZWQBBSPOTO-QMIVOQANSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  21
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 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：

  alpha-甲基葡萄糖甙 、 乙炔 在 氢氧化钾 作用下， 以 甲醇 、 二甲基亚砜 为溶剂， 85.0~87.0 ℃ 、1.82 MPa 条件下， 反应 0.75h， 以75%的产率得到2,3,4,6-tetra(O-vinyl) methyl α-D-glucopyranoside
  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

• A Green and Sustainable Route to Carbohydrate Vinyl Ethers for Accessing Bioinspired Materials with a Unique Microspherical Morphology
  作者：Konstantin S. Rodygin、Irina Werner、Valentine P. Ananikov

  DOI：10.1002/cssc.201701489

  日期：2018.1.10

  and biologically compatible. A green procedure has been developed for the vinylation of carbohydrates by using readily available calcium carbide. Various carbohydrates were utilized as starting materials, resulting in mono‐, di‐, and tetravinyl ethers in high to excellent yields (81–92 %). The synthesized biobased vinyl ethers were utilized as monomers in free radical and cationic polymerizations. A

  从可再生资源合成化学物质和材料是现代科学的主要目标之一。碳水化合物代表了极好的可再生天然原料，具有生态友好性，廉价和生物相容性。通过使用现成的电石，已经开发了一种绿色方法，用于碳水化合物的乙烯基化。各种碳水化合物被用作原料，以高到极好的收率（81–92％）产生单，二和四乙烯基醚。合成的生物基乙烯基醚被用作自由基和阳离子聚合反应的单体。在合成材料中实现了光滑表面和固有微隔室的独特组合。制备了两种类型的生物基材料，其中包括微球和聚合物中的固有中空隔室。
• Schostakowskii et al., Doklady Akademii Nauk SSSR, 1954, vol. 96, p. 99
  作者：Schostakowskii et al.

  DOI：——

  日期：——
• 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.