2-(methacryloyloxy)ethyl 2,3,6-tri-O-benzoyl-4-O-(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-β-D-glucopyranoside | 1318073-94-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(methacryloyloxy)ethyl 2,3,6-tri-O-benzoyl-4-O-(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-β-D-glucopyranoside
• 英文别名: [(2R,3R,4S,5R,6R)-4,5-dibenzoyloxy-6-[2-(2-methylprop-2-enoyloxy)ethoxy]-3-[(2S,3R,4S,5S,6R)-3,4,5-tribenzoyloxy-6-(benzoyloxymethyl)oxan-2-yl]oxyoxan-2-yl]methyl benzoate
• CAS: 1318073-94-7
• 化学式: C₆₇H₅₈O₂₀
• 分子量: 1183.19
• InChiKey: IZKOOQAWVXRAKV-ZBMUESACSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.7
• 重原子数：
  87
• 可旋转键数：
  31
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  247
• 氢给体数：
  0
• 氢受体数：
  20

反应信息

• 作为产物：
  描述：

  甲基丙烯酸羟乙酯 、 [(3aR,5R,6R,7S,7aR)-7-benzoyloxy-2-phenyl-2-prop-2-ynoxy-6-[(2S,3R,4S,5S,6R)-3,4,5-tribenzoyloxy-6-(benzoyloxymethyl)oxan-2-yl]oxy-5,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-b]pyran-5-yl]methyl benzoate 在 gold(III) bromide 作用下， 以 二氯甲烷 为溶剂， 反应 8.0h， 以79%的产率得到2-(methacryloyloxy)ethyl 2,3,6-tri-O-benzoyl-4-O-(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-β-D-glucopyranoside
  参考文献：
  名称：

  Gold catalyzed glycosidations for the synthesis of sugar acrylate/acrylamide hybrids and their utility

  摘要：

  Propargyl glyco 1,2-orthoesters were exploited for the efficient synthesis of interesting glycomonomers such as glyco-acrylates and acrylamides using gold catalysts. It was observed that propargyl glyco 1,2-orthoesters with hydroxyethyl acrylates gives very good yield of the corresponding glyco-acrylates in a single step in the presence of catalytic amount of gold(III) catalyst; whereas, gold catalyzed glycosidation reaction on hydroxyethyl acrylamides was found to yield the corresponding acrylamidoyl 1,2-orthoester which was then converted to the corresponding glycol-acrylamide in the presence of catalytic amount of TMSOTf. Synthesized glyco-acrylate/acrylamide monomers are shown to undergo thiolate addition as well as free radical polymerization (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2011.04.018

文献信息

• Gold catalyzed glycosidations for the synthesis of sugar acrylate/acrylamide hybrids and their utility
  作者：Shivaji A. Thadke、Mritunjoy Kar、Sayam Sen Gupta、Srinivas Hotha

  DOI：10.1016/j.carres.2011.04.018

  日期：2011.9

  Propargyl glyco 1,2-orthoesters were exploited for the efficient synthesis of interesting glycomonomers such as glyco-acrylates and acrylamides using gold catalysts. It was observed that propargyl glyco 1,2-orthoesters with hydroxyethyl acrylates gives very good yield of the corresponding glyco-acrylates in a single step in the presence of catalytic amount of gold(III) catalyst; whereas, gold catalyzed glycosidation reaction on hydroxyethyl acrylamides was found to yield the corresponding acrylamidoyl 1,2-orthoester which was then converted to the corresponding glycol-acrylamide in the presence of catalytic amount of TMSOTf. Synthesized glyco-acrylate/acrylamide monomers are shown to undergo thiolate addition as well as free radical polymerization (C) 2011 Elsevier Ltd. All rights reserved.