2-(acryloyloxy)ethyl 2,3,4,6-tetra-O-benzoyl-α-D-mannopyranoside | 1318073-87-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-(acryloyloxy)ethyl 2,3,4,6-tetra-O-benzoyl-α-D-mannopyranoside
• 英文别名: [(2R,3R,4S,5S,6S)-3,4,5-tribenzoyloxy-6-(2-prop-2-enoyloxyethoxy)oxan-2-yl]methyl benzoate
• CAS: 1318073-87-8
• 化学式: C₃₉H₃₄O₁₂
• 分子量: 694.692
• InChiKey: PBWZDPUCZAOHLW-RTHJKYTLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  51
• 可旋转键数：
  19
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  150
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  2-(acryloyloxy)ethyl 2,3,4,6-tetra-O-benzoyl-α-D-mannopyranoside 、 N-[(tert-butoxy)carbonyl]-L-cysteine methyl ester 在 三乙胺 作用下， 以 乙醇 为溶剂， 反应 8.0h， 以81%的产率得到(2R,3R,4S,5S,6S)-2-((benzoyloxy)methyl)-6-(((R)-6-(methoxycarbonyl)-2,2-dimethyl-4,11-dioxo-3,12-dioxa-8-thia-5-azatetradecan-14-yl)oxy)tetrahydro-2H-pyran-3,4,5-triyl tribenzoate
  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
• 作为产物：
  描述：

  3,4,6-tri-o-benzoyl-1,2-o-propynylorthobenzoyl-β-D-mannopyranose 、 丙烯酸羟乙酯 在 gold(III) bromide 作用下， 以 二氯甲烷 为溶剂， 反应 10.0h， 以78%的产率得到2-(acryloyloxy)ethyl 2,3,4,6-tetra-O-benzoyl-α-D-mannopyranoside
  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.