3-ethoxycarbonyl-2-methyl-5-(2',3'-O-sulfonyl-α-D-erythrofuranosyl)furan | 426818-68-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - Benzoxathioles
• 英文名称: 3-ethoxycarbonyl-2-methyl-5-(2',3'-O-sulfonyl-α-D-erythrofuranosyl)furan
• 英文别名: ethyl 5-[(3aS,4S,6aR)-2,2-dioxo-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3,2]dioxathiol-4-yl]-2-methylfuran-3-carboxylate
• CAS: 426818-68-0
• 化学式: C₁₂H₁₄O₈S
• 分子量: 318.304
• InChiKey: MQNRHVCFQIGFNG-GMTAPVOTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  110
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  3-ethoxycarbonyl-2-methyl-5-(2',3'-O-sulfonyl-α-D-erythrofuranosyl)furan 在 吡啶 、 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 5-(2'-O-acetyl-3'-azido-3'-deoxy-β-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
• 作为产物：
  描述：

  ethyl 5-((2S,3S,4R)-3,4-dihydroxytetrahydrofuran-2-yl)-2-methylfuran-3-carboxylate 在 磺酰氯 、 三乙胺 作用下， 以 乙酸乙酯 为溶剂， 反应 3.5h， 以1.48 g的产率得到3-ethoxycarbonyl-2-methyl-5-(2',3'-O-sulfonyl-β-D-erythrofuranosyl)furan
  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