N-[2-O-acetyl-1,3-dideoxy-1-(3'-acetyl-2'-methylpyrrole-5'-yl)-α-L-threofuranos-3-yl]-N'-[2''-O-acetyl-1'',3''-dideoxy-1''-(3'''-ethoxycarbonyl-2'''-methylfur-5'''-yl)-α-L-threofuranos-3''-yl]thiourea | 426819-21-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: N-[2-O-acetyl-1,3-dideoxy-1-(3'-acetyl-2'-methylpyrrole-5'-yl)-α-L-threofuranos-3-yl]-N'-[2''-O-acetyl-1'',3''-dideoxy-1''-(3'''-ethoxycarbonyl-2'''-methylfur-5'''-yl)-α-L-threofuranos-3''-yl]thiourea
• 英文别名: ethyl 5-[(2R,3R,4S)-4-[[(3S,4R,5S)-5-(4-acetyl-5-methyl-1H-pyrrol-2-yl)-4-acetyloxyoxolan-3-yl]carbamothioylamino]-3-acetyloxyoxolan-2-yl]-2-methylfuran-3-carboxylate
• CAS: 426819-21-8
• 化学式: C₂₈H₃₅N₃O₁₀S
• 分子量: 605.666
• InChiKey: VSAQCBNZAYHRMD-MTCGBIPFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  42
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  200
• 氢给体数：
  3
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  N-[2-O-acetyl-1,3-dideoxy-1-(3'-acetyl-2'-methylpyrrole-5'-yl)-α-L-threofuranos-3-yl]-N'-[2''-O-acetyl-1'',3''-dideoxy-1''-(3'''-ethoxycarbonyl-2'''-methylfur-5'''-yl)-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-[1,3-dideoxy-1-(3'-acetyl-2'-methylpyrrole-5'-yl)-α-L-threofuranos-3-yl]-N'-[1'',3''-dideoxy-1''-(3'''-ethoxycarbonyl-2'''-methylfur-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：

  ethyl 5-((2S,3S,4R)-3,4-dihydroxytetrahydrofuran-2-yl)-2-methylfuran-3-carboxylate 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 、 丙酮 为溶剂， 40.0 ℃ 、101.33 kPa 条件下， 反应 7.5h， 生成 N-[2-O-acetyl-1,3-dideoxy-1-(3'-acetyl-2'-methylpyrrole-5'-yl)-α-L-threofuranos-3-yl]-N'-[2''-O-acetyl-1'',3''-dideoxy-1''-(3'''-ethoxycarbonyl-2'''-methylfur-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