(6R,7S,8S)-2,3-diphenyl-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine-6,7,8-triol | 1213264-75-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: (6R,7S,8S)-2,3-diphenyl-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine-6,7,8-triol
• CAS: 1213264-75-5
• 化学式: C₁₉H₁₈N₂O₃
• 分子量: 322.364
• InChiKey: UAKXUTMMGJKOFJ-FHLIZLRMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  78.5
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  D-木糖 、 安息香精油 在 ammonium acetate 、 草酸 作用下， 反应 0.18h， 以95%的产率得到(6R,7S,8S)-2,3-diphenyl-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine-6,7,8-triol
  参考文献：
  名称：

  Efficient one-pot synthetic protocols for iminosugar-bearing imidazo[1,2-a]pyridines from carbohydrates

  摘要：

  This letter describes two unprecedented one-pot high yielding synthetic approaches to imidazo[1,2-a]pyridine scaffolds from carbohydrates. The first approach involves microwave-assisted acid-catalyzed domino reactions of unprotected D-glucose/D-xylose with ammonium acetate and benzoin to afford polyhydroxy iminosugar-bearing tetrahydroimidazo[1,2-a]pyridines. In the second approach, polyhydroxy iminosugar-bearing tetrahydrobenzimidazo[1,2-a]pyridines were synthesized by using unprotected D-glucose/D-xylose and 1,2-diamines in the presence of 10 mol % of oxalic acid under solvent-free microwave irradiation conditions. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2009.11.016

文献信息

• Efficient one-pot synthetic protocols for iminosugar-bearing imidazo[1,2-a]pyridines from carbohydrates
  作者：Lal Dhar S. Yadav、Chhama Awasthi

  DOI：10.1016/j.carres.2009.11.016

  日期：2010.1

  This letter describes two unprecedented one-pot high yielding synthetic approaches to imidazo[1,2-a]pyridine scaffolds from carbohydrates. The first approach involves microwave-assisted acid-catalyzed domino reactions of unprotected D-glucose/D-xylose with ammonium acetate and benzoin to afford polyhydroxy iminosugar-bearing tetrahydroimidazo[1,2-a]pyridines. In the second approach, polyhydroxy iminosugar-bearing tetrahydrobenzimidazo[1,2-a]pyridines were synthesized by using unprotected D-glucose/D-xylose and 1,2-diamines in the presence of 10 mol % of oxalic acid under solvent-free microwave irradiation conditions. (C) 2009 Elsevier Ltd. All rights reserved.