2,6,7-Trichloro-5-(α-D-ribofuranosyl)imidazo[1,2-a]pyridine

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,6,7-Trichloro-5-(α-D-ribofuranosyl)imidazo[1,2-a]pyridine
• 英文别名: (2R,3S,4R,5R)-2-(hydroxymethyl)-5-(2,6,7-trichloroimidazo[1,2-a]pyridin-5-yl)tetrahydrofuran-3,4-diol；(2R,3S,4R,5R)-2-(hydroxymethyl)-5-(2,6,7-trichloroimidazo[1,2-a]pyridin-5-yl)oxolane-3,4-diol
• 化学式: C₁₂H₁₁Cl₃N₂O₄
• 分子量: 353.589
• InChiKey: LETVLOJWSLRUFP-AYAMHAMTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  87.2
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2,6,7-trichloro-5-[5-O-(tert-butyldimethylsilyl)-1-acetoxy-2,3-O-isopropylidene-α-D-ribofuranosyl]imidazo[1,2-a]pyridine 在 盐酸 、 三乙基硅烷 、 三氟甲磺酸三甲基硅酯 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 24.0h， 生成 2,6,7-Trichloro-5-(α-D-ribofuranosyl)imidazo[1,2-a]pyridine
  参考文献：
  名称：

  Synthesis of Imidazo[1,2-a]pyridine C-Nucleosides with an Unexpected Site of Ribosylation

  摘要：

  Several new polychlorinated imidazo[1,2-alpha]pyridine C-nucleosides have been prepared. Lithiated imidazo[1,2-alpha]pyridines were condensed with protected ribonolactones, trapped as 1'-acetoxy derivatives, and these 1'-acetoxy derivatives were reductively deacetoxylated and deprotected to give C-nucleosides. Long-range proton-carbon decoupling experiments were used to determine the actual site of ribosylation and established that the ribose moiety was unexpectedly attached to the C5 position of the imidazo[1,2-alpha]pyridines. This method has provided C-nucleosides, such as 2,6-dichloro-5-(beta-D-ribofuranosyl)imidazo[1,2-alpha]pyridine and 2,6,7-trichloro-5-(beta-D-ribofuranosyl)imidazo[1,2-alpha]pyridine and the corresponding alpha-products.

  DOI：

  10.1021/jo9619342

文献信息

• US6214801B1
  申请人：——

  公开号：US6214801B1

  公开（公告）日：2001-04-10
• Synthesis of Imidazo[1,2-<i>a</i>]pyridine C-Nucleosides with an Unexpected Site of Ribosylation
  作者：Kristjan S. Gudmundsson、John C. Drach、Leroy B. Townsend

  DOI：10.1021/jo9619342

  日期：1997.5.1

  Several new polychlorinated imidazo[1,2-alpha]pyridine C-nucleosides have been prepared. Lithiated imidazo[1,2-alpha]pyridines were condensed with protected ribonolactones, trapped as 1'-acetoxy derivatives, and these 1'-acetoxy derivatives were reductively deacetoxylated and deprotected to give C-nucleosides. Long-range proton-carbon decoupling experiments were used to determine the actual site of ribosylation and established that the ribose moiety was unexpectedly attached to the C5 position of the imidazo[1,2-alpha]pyridines. This method has provided C-nucleosides, such as 2,6-dichloro-5-(beta-D-ribofuranosyl)imidazo[1,2-alpha]pyridine and 2,6,7-trichloro-5-(beta-D-ribofuranosyl)imidazo[1,2-alpha]pyridine and the corresponding alpha-products.