[(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 | 1318074-12-2

• 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: [(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
• CAS: 1318074-12-2
• 化学式: C₄₈H₅₂N₂O₁₅S
• 分子量: 929.011
• InChiKey: FJGNHFUCWHCSGK-WBMKRXRXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  66
• 可旋转键数：
  27
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  243
• 氢给体数：
  2
• 氢受体数：
  16

反应信息

• 作为产物：
  描述：

  3,4,6-tri-o-benzoyl-1,2-o-propynylorthobenzoyl-β-D-mannopyranose 在 gold(III) bromide 、 三氟甲磺酸三甲基硅酯 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 18.08h， 生成 [(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

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.