N,N'-bis[2-O-acetyl-1-(3'-acetyl-2'-methylpyrrole-5'-yl)-1,3-dideoxy-α-L-threofuranos-3-yl]thiourea | 426819-19-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: N,N'-bis[2-O-acetyl-1-(3'-acetyl-2'-methylpyrrole-5'-yl)-1,3-dideoxy-α-L-threofuranos-3-yl]thiourea
• 英文别名: [(2S,3R,4S)-2-(4-acetyl-5-methyl-1H-pyrrol-2-yl)-4-[[(3S,4R,5S)-5-(4-acetyl-5-methyl-1H-pyrrol-2-yl)-4-acetyloxyoxolan-3-yl]carbamothioylamino]oxolan-3-yl] acetate
• CAS: 426819-19-4
• 化学式: C₂₇H₃₄N₄O₈S
• 分子量: 574.655
• InChiKey: SJRSENWEJBEVFB-MGEKTERKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  40
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  193
• 氢给体数：
  4
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  N,N'-bis[2-O-acetyl-1-(3'-acetyl-2'-methylpyrrole-5'-yl)-1,3-dideoxy-α-L-threofuranos-3-yl]thiourea 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 0.25h， 以100%的产率得到N,N'-bis[1,3-dideoxy-1-(3'-acetyl-2'-methylpyrrole-5'-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：

  3-acetyl-5-(2'-O-acetyl-3'-azido-3'-deoxy-α/β-L-threofuranosyl)-2-methylpyrrole 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 、 二氯甲烷 、 丙酮 为溶剂， 20.0~40.0 ℃ 、101.33 kPa 条件下， 反应 6.5h， 生成 N,N'-bis[2-O-acetyl-1-(3'-acetyl-2'-methylpyrrole-5'-yl)-1,3-dideoxy-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