4-(2'-O-acetyl-3'-deoxy-3'-isothiocyanato-α-L-threofuranosyl)-1,3-dihydro-3-methyl-1-p-tolyl-2H-imidazole-2-thione | 426819-14-9

• 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-(2'-O-acetyl-3'-deoxy-3'-isothiocyanato-α-L-threofuranosyl)-1,3-dihydro-3-methyl-1-p-tolyl-2H-imidazole-2-thione
• 英文别名: [(2S,3R,4S)-4-isothiocyanato-2-[3-methyl-1-(4-methylphenyl)-2-sulfanylideneimidazol-4-yl]oxolan-3-yl] acetate
• CAS: 426819-14-9
• 化学式: C₁₈H₁₉N₃O₃S₂
• 分子量: 389.499
• InChiKey: JXBBLNSESARORD-UAGQMJEPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  119
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-(2'-O-acetyl-3'-deoxy-3'-isothiocyanato-α-L-threofuranosyl)-1,3-dihydro-3-methyl-1-p-tolyl-2H-imidazole-2-thione 在 sodium methylate 作用下， 以 甲醇 、 丙酮 为溶剂， 反应 12.08h， 生成 N,N'-bis[1,3-dideoxy-1-(1',3'-dihydro-3'-methyl-2'-thioxo-1'-p-tolyl-2'-H-imidazole-4'-yl)-α-L-threofuranos-3-yl]thiourea
  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：

  4-((2S,3R,4R)-3,4-Dihydroxy-tetrahydro-furan-2-yl)-3-methyl-1-p-tolyl-1,3-dihydro-imidazole-2-thione 在 palladium on activated charcoal 吡啶 、 sodium azide 、 磺酰氯 、 氢气 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 14.0h， 生成 4-(2'-O-acetyl-3'-deoxy-3'-isothiocyanato-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