4-amino-6-bromo-5-cyano-7-(2,3-di-O-benzoyl-5-deoxy-5-fluoro-β-D-ribofuranosyl)pyrrolo<2,3-d>pyrimidine | 174019-77-3

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 吡咯并嘧啶核苷和核苷酸
• 英文名称: 4-amino-6-bromo-5-cyano-7-(2,3-di-O-benzoyl-5-deoxy-5-fluoro-β-D-ribofuranosyl)pyrrolo<2,3-d>pyrimidine
• 英文别名: [(2S,3S,4R,5R)-5-(4-amino-6-bromo-5-cyanopyrrolo[2,3-d]pyrimidin-7-yl)-4-benzoyloxy-2-(fluoromethyl)oxolan-3-yl] benzoate
• CAS: 174019-77-3
• 化学式: C₂₆H₁₉BrFN₅O₅
• 分子量: 580.37
• InChiKey: JXAGQFRJZOQNLB-AGFSROSKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  38
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  142
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  4-amino-6-bromo-5-cyano-7-(2,3-di-O-benzoyl-5-deoxy-5-fluoro-β-D-ribofuranosyl)pyrrolo<2,3-d>pyrimidine 在 palladium on activated charcoal 氢气 、 三乙胺 作用下， 以 1,4-二氧六环 为溶剂， 反应 24.0h， 以90%的产率得到4-amino-5-cyano-7-(2,3-di-O-benzoyl-5-deoxy-5-fluoro-β-D-ribofuranosyl)pyrrolo<2,3-d>pyrimidine
  参考文献：
  名称：

  Synthesis of 5′-Fluoro-5′-deoxy-and 5′-Amino-5′-Deoxytoyocamycin and Sangivamycin and Some Related Derivatives

  摘要：

  A series of 5'-substituted analogs of toyocamycin were prepared by condensation of silylated 4-amino-6-bromo-5-cyanopyrrolo[2,3-d]pyrimidine with protected 5-azidod-deoxy- or 5-fluoro-5-deoxyribofuranose followed by debromination and deblocking. Alternatively, 5'-azido-5'-deoxytoyocamycin was prepared by azidation of toyocamycin. Conversion of the 5-nitrile function of the toyocamycin derivatives into a carboxamide or a thiocarboxamide gave the corresponding analogs of sangivamycin or thiosangivamycin while reduction of the 5'-azido-5'-deoxy nucleosides provided 5'-amino-5'-deoxy derivatives.

  DOI：

  10.1080/15257779508010707
• 作为产物：
  描述：

  methyl 5-deoxy-5-fluoro-β-D-ribofuranoside 在 吡啶 、 三甲基氯硅烷 、 TMSTf 、 硫酸 、 六甲基二硅氮烷 作用下， 以 溶剂黄146 为溶剂， 反应 41.0h， 生成 4-amino-6-bromo-5-cyano-7-(2,3-di-O-benzoyl-5-deoxy-5-fluoro-β-D-ribofuranosyl)pyrrolo<2,3-d>pyrimidine
  参考文献：
  名称：

  Synthesis of 5′-Fluoro-5′-deoxy-and 5′-Amino-5′-Deoxytoyocamycin and Sangivamycin and Some Related Derivatives

  摘要：

  A series of 5'-substituted analogs of toyocamycin were prepared by condensation of silylated 4-amino-6-bromo-5-cyanopyrrolo[2,3-d]pyrimidine with protected 5-azidod-deoxy- or 5-fluoro-5-deoxyribofuranose followed by debromination and deblocking. Alternatively, 5'-azido-5'-deoxytoyocamycin was prepared by azidation of toyocamycin. Conversion of the 5-nitrile function of the toyocamycin derivatives into a carboxamide or a thiocarboxamide gave the corresponding analogs of sangivamycin or thiosangivamycin while reduction of the 5'-azido-5'-deoxy nucleosides provided 5'-amino-5'-deoxy derivatives.

  DOI：

  10.1080/15257779508010707