(E)-1-(tert-Butyl-diphenyl-silanyloxy)-5-(2,6-dichloro-imidazo[1,2-a]pyridin-3-yl)-pent-4-en-2-ol | 194228-75-6

• 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: (E)-1-(tert-Butyl-diphenyl-silanyloxy)-5-(2,6-dichloro-imidazo[1,2-a]pyridin-3-yl)-pent-4-en-2-ol
• 英文别名: (E)-1-[tert-butyl(diphenyl)silyl]oxy-5-(2,6-dichloroimidazo[1,2-a]pyridin-3-yl)pent-4-en-2-ol
• CAS: 194228-75-6
• 化学式: C₂₈H₃₀Cl₂N₂O₂Si
• 分子量: 525.55
• InChiKey: DJEFVRWNCXSAOO-MHWRWJLKSA-N

物化性质

• 熔点：
  155-156 °C
• 密度：
  1.17±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.98
• 重原子数：
  35
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  46.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-1-(tert-Butyl-diphenyl-silanyloxy)-5-(2,6-dichloro-imidazo[1,2-a]pyridin-3-yl)-pent-4-en-2-ol 在 2,6-二甲基吡啶 、 碘 、 potassium carbonate 、 三乙胺 、 叔丁醇 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 2.5h， 生成 3-[(2S,3R,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-3-iodo-tetrahydro-furan-2-yl]-2,6-dichloro-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
• 作为产物：
  描述：

  [2-(2,2-dimethyl-[1,3]dioxolan-4-yl)-ethyl]-(triphenyl)-phosphonium iodide 在 吡啶 、 4-二甲氨基吡啶 、 水 、 4-甲基苯磺酸吡啶 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 24.0h， 生成 (E)-1-(tert-Butyl-diphenyl-silanyloxy)-5-(2,6-dichloro-imidazo[1,2-a]pyridin-3-yl)-pent-4-en-2-ol
  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