5-(2'-O-acetyl-3'-azido-3'-deoxy-β-L-threofuranosyl)-3-ethoxycarbonyl-2-methylfuran | 426818-97-5

• 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'-azido-3'-deoxy-β-L-threofuranosyl)-3-ethoxycarbonyl-2-methylfuran
• 英文别名: ethyl 5-[(2S,3R,4S)-3-acetyloxy-4-azidooxolan-2-yl]-2-methylfuran-3-carboxylate
• CAS: 426818-97-5
• 化学式: C₁₄H₁₇N₃O₆
• 分子量: 323.305
• InChiKey: YBEABHDEKJKZGW-CYZMBNFOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  89.3
• 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'-azido-3'-deoxy-β-L-threofuranosyl)-3-ethoxycarbonyl-2-methylfuran 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 0.25h， 以83%的产率得到5-(2'-O-acetyl-3'-amino-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：

  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