4,4'-bis(α-D-mannopyranosyloxy)biphenyl | 1318797-50-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4,4'-bis(α-D-mannopyranosyloxy)biphenyl
• 英文别名: (2R,3S,4S,5S,6R)-2-(hydroxymethyl)-6-[4-[4-[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]phenoxy]oxane-3,4,5-triol
• CAS: 1318797-50-0
• 化学式: C₂₄H₃₀O₁₂
• 分子量: 510.495
• InChiKey: FHMAENUHOXZAME-PUYHWVFISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  36
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  199
• 氢给体数：
  8
• 氢受体数：
  12

反应信息

• 作为产物：
  描述：

  p-iodophenyl 2,3,4,6-tetra-O-acetyl α-D-mannopyranoside 在 四(三苯基膦)钯 、 四丁基溴化铵 、 sodium methylate 、 potassium acetate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 14.0h， 生成 4,4'-bis(α-D-mannopyranosyloxy)biphenyl
  参考文献：
  名称：

  Palladium-Catalyzed Ullmann-Type Reductive Homocoupling of Iodoaryl Glycosides

  摘要：

  A catalytic synthesis of novel biaryl-linked divalent glycosides was achieved using an electroreductive palladium-catalyzed iodoaryl-iodoaryl coupling reaction. This new method was optimized for the synthesis of divalent biaryl-linked mannopyranosides that was subsequently generalized toward several carbohydrate substrates with yields up to 96%.

  DOI：

  10.1021/jo2025652

文献信息

• Synthesis of a small library of bivalent α-d-mannopyranosides for lectin cross-linking
  作者：Milan Bergeron-Brlek、Tze Chieh Shiao、M. Corazon Trono、René Roy

  DOI：10.1016/j.carres.2011.03.041

  日期：2011.9

  A small library of bivalent alpha-D-mannopyranosides having rigid linkers was constructed in order to evaluate the effects of inter-saccharide distances upon multivalent binding interactions with plant and bacterial lectins. To this end, iodoaryl and propargyl alpha-D-mannopyranosides were synthesized and the former treated with TMS-acetylene under palladium chemistry to provide their corresponding ethynylaryl derivatives. A library of 15 dimeric members was then obtained using Lewis acid catalyzed glycosidation, aryl-aryl homocoupling, transition metal catalyzed Sonogashira cross-coupling reactions, and oxidative Glaser homocoupling. (C) 2011 Elsevier Ltd. All rights reserved.
• Palladium-Catalyzed Ullmann-Type Reductive Homocoupling of Iodoaryl Glycosides
  作者：Milan Bergeron-Brlek、Denis Giguère、Tze Chieh Shiao、Catherine Saucier、René Roy

  DOI：10.1021/jo2025652

  日期：2012.3.16

  A catalytic synthesis of novel biaryl-linked divalent glycosides was achieved using an electroreductive palladium-catalyzed iodoaryl-iodoaryl coupling reaction. This new method was optimized for the synthesis of divalent biaryl-linked mannopyranosides that was subsequently generalized toward several carbohydrate substrates with yields up to 96%.