2-(acrylamido)ethyl 2,3,4,6-tetra-O-benzoyl-α-D-mannopyranoside | 1318073-99-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 2-(acrylamido)ethyl 2,3,4,6-tetra-O-benzoyl-α-D-mannopyranoside
• CAS: 1318073-99-2
• 化学式: C₃₉H₃₅NO₁₁
• 分子量: 693.707
• InChiKey: KSELYXWKJKFHDN-RTHJKYTLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.56
• 重原子数：
  51.0
• 可旋转键数：
  14.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  152.76
• 氢给体数：
  1.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  2-(acrylamido)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90%的产率得到[(2R,3R,4S,5S,6S)-3,4,5-tribenzoyloxy-6-[2-[3-[(2R)-3-methoxy-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-oxopropyl]sulfanylpropanoylamino]ethoxy]oxan-2-yl]methyl benzoate
  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-[(2-acrylamidoethoxy)phenylmethylene]-β-D-mannopyranoside 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 0.08h， 生成 2-(acrylamido)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