4-(3'-azido-3'-deoxy-α-L-threofuranosyl)-1,3-dihydro-3-methyl-1-p-tolyl-2H-imidazole-2-thione | 426818-85-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-(3'-azido-3'-deoxy-α-L-threofuranosyl)-1,3-dihydro-3-methyl-1-p-tolyl-2H-imidazole-2-thione
• 英文别名: 4-[(2S,3R,4S)-4-azido-3-hydroxyoxolan-2-yl]-3-methyl-1-(4-methylphenyl)imidazole-2-thione
• CAS: 426818-85-1
• 化学式: C₁₅H₁₇N₅O₂S
• 分子量: 331.398
• InChiKey: GGTXVLGBRAFAJW-YUTCNCBUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  82.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-(3'-azido-3'-deoxy-α-L-threofuranosyl)-1,3-dihydro-3-methyl-1-p-tolyl-2H-imidazole-2-thione 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 15.0h， 以81%的产率得到4-(3'-amino-3'-deoxy-α-L-threofuranosyl)-1,3-dihydro-3-methyl-1-p-tolyl-2H-imidazole-2-thione
  参考文献：
  名称：

  Fluoronucleosides, Isothiocyanato C-Nucleosides, and Thioureylene Di-C-nucleosides via Cyclic Sulfates

  摘要：

  Cyclic sulfates of N- and C-nucleosides (D-ribo and D-erythro configurations, respectively) are used to prepare T-fluoro and 3'-azido D-xylo N-nucleosides and L-threo C-nucleosides. The reduction of the 3'-azido C-nucleosides (furan, imidazoline-2-thione, and pyrrole derivatives) gives T-amino C-nucleosides, which, by reaction with thiocarbonyldiimidazole, are transformed into T-isothiocyanato C-nucleosides. Reaction of the 3'-amino with the T-isothiocyanato C-nucleosides gives thioureylene di-C-nucleosides, a type of nucleotide analogue with a nonionic bridge isosteric of the phosphate group.

  DOI：

  10.1021/jo0110303
• 作为产物：
  描述：

  1,3-dihydro-3-methyl-4-(2',3'-O-sulfonyl-β-D-erythrofuranosyl)-1-p-tolyl-2H-imidazole-2-thione 在 sodium azide 、 硫酸 作用下， 以 N,N-二甲基甲酰胺 、 水 为溶剂， 反应 2.5h， 以74%的产率得到4-(3'-azido-3'-deoxy-α-L-threofuranosyl)-1,3-dihydro-3-methyl-1-p-tolyl-2H-imidazole-2-thione
  参考文献：
  名称：

  Fluoronucleosides, Isothiocyanato C-Nucleosides, and Thioureylene Di-C-nucleosides via Cyclic Sulfates

  摘要：

  Cyclic sulfates of N- and C-nucleosides (D-ribo and D-erythro configurations, respectively) are used to prepare T-fluoro and 3'-azido D-xylo N-nucleosides and L-threo C-nucleosides. The reduction of the 3'-azido C-nucleosides (furan, imidazoline-2-thione, and pyrrole derivatives) gives T-amino C-nucleosides, which, by reaction with thiocarbonyldiimidazole, are transformed into T-isothiocyanato C-nucleosides. Reaction of the 3'-amino with the T-isothiocyanato C-nucleosides gives thioureylene di-C-nucleosides, a type of nucleotide analogue with a nonionic bridge isosteric of the phosphate group.

  DOI：

  10.1021/jo0110303