2,6,7-Trichloro-3-(1,2(S)-dihydroxy-pent-4(E)-en-5-yl)imidazo[1,2-a]pyridine | 194228-87-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并吡啶类
• 英文名称: 2,6,7-Trichloro-3-(1,2(S)-dihydroxy-pent-4(E)-en-5-yl)imidazo[1,2-a]pyridine
• 英文别名: (E,2S)-5-(2,6,7-trichloroimidazo[1,2-a]pyridin-3-yl)pent-4-ene-1,2-diol
• CAS: 194228-87-0
• 化学式: C₁₂H₁₁Cl₃N₂O₂
• 分子量: 321.591
• InChiKey: DKMHCRWJYPAHBJ-RMKMGNDCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  57.8
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,6,7-Trichloro-3-(1,2(S)-dihydroxy-pent-4(E)-en-5-yl)imidazo[1,2-a]pyridine 在 碘 、 potassium carbonate 作用下， 生成 (3S,5S,6R)-5-Iodo-6-(2,6,7-trichloro-imidazo[1,2-a]pyridin-3-yl)-tetrahydro-pyran-3-ol 、 2,6,7-Trichloro-3-(2,3-dideoxy-2-iodo-β-D-ribofuranosyl)imidazo[1,2-a]pyridine 、 [(2S,4S,5R)-4-Iodo-5-(2,6,7-trichloro-imidazo[1,2-a]pyridin-3-yl)-tetrahydro-furan-2-yl]-methanol
  参考文献：
  名称：

  Synthesis of the First C3 Ribosylated Imidazo[1,2-a]pyridine C-Nucleoside by Enantioselective Construction of the Ribose Moiety

  摘要：

  The metabolic instability of the glycosidic linkage in 2,5,6-trichloro-1-(beta-D-ribofuranosyl)benzimidazole prompted us to synthesize the structurally related C-nucleoside 2,6,7-trichloro-3-(beta-D-ribofuranosyl)imidazo[1,2-a]pyridine. Synthesis of this first C3-ribofuranosylimidazo[1,2-a]pyridine was accomplished by developing a modification of existing iodocyclization methodology for obtaining a 1',4'-syn furanosyl precursor, without an extensive protection scheme. This 1',4'-syn precursor was elaborated inter the desired ribofuranosyl C-nucleoside. X-ray crystallography was used to unambiguously determine structure and absolute stereochemistry of this C-nucleoside.

  DOI：

  10.1021/jo9711145
• 作为产物：
  描述：

  2,6,7-trichloro-3-formylmethylimidazo[1,2-a]pyridine 在 正丁基锂 、 水 、 4-甲基苯磺酸吡啶 作用下， 以 甲醇 为溶剂， 反应 25.17h， 生成 2,6,7-Trichloro-3-(1,2(S)-dihydroxy-pent-4(E)-en-5-yl)imidazo[1,2-a]pyridine
  参考文献：
  名称：

  Synthesis of the First C3 Ribosylated Imidazo[1,2-a]pyridine C-Nucleoside by Enantioselective Construction of the Ribose Moiety

  摘要：

  The metabolic instability of the glycosidic linkage in 2,5,6-trichloro-1-(beta-D-ribofuranosyl)benzimidazole prompted us to synthesize the structurally related C-nucleoside 2,6,7-trichloro-3-(beta-D-ribofuranosyl)imidazo[1,2-a]pyridine. Synthesis of this first C3-ribofuranosylimidazo[1,2-a]pyridine was accomplished by developing a modification of existing iodocyclization methodology for obtaining a 1',4'-syn furanosyl precursor, without an extensive protection scheme. This 1',4'-syn precursor was elaborated inter the desired ribofuranosyl C-nucleoside. X-ray crystallography was used to unambiguously determine structure and absolute stereochemistry of this C-nucleoside.

  DOI：

  10.1021/jo9711145

文献信息

• US6214801B1
  申请人：——

  公开号：US6214801B1

  公开（公告）日：2001-04-10
• Synthesis of the First C3 Ribosylated Imidazo[1,2-<i>a</i>]pyridine C-Nucleoside by Enantioselective Construction of the Ribose Moiety
  作者：Kristjan S. Gudmundsson、John C. Drach、Leroy B. Townsend

  DOI：10.1021/jo9711145

  日期：1998.2.1

  The metabolic instability of the glycosidic linkage in 2,5,6-trichloro-1-(beta-D-ribofuranosyl)benzimidazole prompted us to synthesize the structurally related C-nucleoside 2,6,7-trichloro-3-(beta-D-ribofuranosyl)imidazo[1,2-a]pyridine. Synthesis of this first C3-ribofuranosylimidazo[1,2-a]pyridine was accomplished by developing a modification of existing iodocyclization methodology for obtaining a 1',4'-syn furanosyl precursor, without an extensive protection scheme. This 1',4'-syn precursor was elaborated inter the desired ribofuranosyl C-nucleoside. X-ray crystallography was used to unambiguously determine structure and absolute stereochemistry of this C-nucleoside.