5-(2'-O-acetyl-3'-deoxy-3'-isothiocyanato-α-L-threofuranosyl)-3-ethoxycarbonyl-2-methylfuran | 426819-11-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃
• 英文名称: 5-(2'-O-acetyl-3'-deoxy-3'-isothiocyanato-α-L-threofuranosyl)-3-ethoxycarbonyl-2-methylfuran
• 英文别名: ethyl 5-[(2R,3R,4S)-3-acetyloxy-4-isothiocyanatooxolan-2-yl]-2-methylfuran-3-carboxylate
• CAS: 426819-11-6
• 化学式: C₁₅H₁₇NO₆S
• 分子量: 339.369
• InChiKey: AVUGBLAMTBOELB-YUTCNCBUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  119
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  5-(2'-O-acetyl-3'-deoxy-3'-isothiocyanato-α-L-threofuranosyl)-3-ethoxycarbonyl-2-methylfuran 在 sodium methylate 作用下， 以 甲醇 、 丙酮 为溶剂， 反应 12.25h， 生成 N-[1,3-dideoxy-1-(1',3'-dihydro-3'-methyl-2'-thioxo-1'-p-tolyl-2'H-imidazole-4'-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 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 6.5h， 生成 5-(2'-O-acetyl-3'-deoxy-3'-isothiocyanato-α-L-threofuranosyl)-3-ethoxycarbonyl-2-methylfuran
  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