2,2'-bis-(α-D-mannopyranosyloxy)biphenyl | 1364510-96-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,2'-bis-(α-D-mannopyranosyloxy)biphenyl
• 英文别名: (2R,3S,4S,5S,6R)-2-(hydroxymethyl)-6-[2-[2-[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]phenoxy]oxane-3,4,5-triol
• CAS: 1364510-96-2
• 化学式: C₂₄H₃₀O₁₂
• 分子量: 510.495
• InChiKey: RWPIJKLTVUWUKG-PUYHWVFISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 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：

  2-iodophenyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside 在 四丁基溴化铵 、 sodium methylate 、 palladium diacetate 、 三乙胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 38.0h， 生成 2,2'-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

• 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%.