5-(3'-amino-2'-O-benzyl-3'-deoxy-α-L-threofuranosyl)-3-ethoxycarbonyl-2-methylfuran | 426818-92-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-(3'-amino-2'-O-benzyl-3'-deoxy-α-L-threofuranosyl)-3-ethoxycarbonyl-2-methylfuran
• 英文别名: ethyl 5-[(2R,3R,4S)-4-amino-3-phenylmethoxyoxolan-2-yl]-2-methylfuran-3-carboxylate
• CAS: 426818-92-0
• 化学式: C₁₉H₂₃NO₅
• 分子量: 345.395
• InChiKey: CKUJJZIMCZPMID-JQHSSLGASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  83.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N,N'-硫羰基二咪唑 、 5-(3'-amino-2'-O-benzyl-3'-deoxy-α-L-threofuranosyl)-3-ethoxycarbonyl-2-methylfuran 以 二氯甲烷 为溶剂， 反应 10.0h， 以69%的产率得到5-(2'-O-benzyl-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
• 作为产物：
  描述：

  5-(3'-azido-2'-O-benzyl-3'-deoxy-α-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 1.0h， 以69%的产率得到5-(3'-amino-2'-O-benzyl-3'-deoxy-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