4-amino-5-cyano-7-(5-deoxy-5-fluoro-β-D-ribofuranosyl)pyrrolo<2,3-d>pyrimidine | 155637-31-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-amino-5-cyano-7-(5-deoxy-5-fluoro-β-D-ribofuranosyl)pyrrolo<2,3-d>pyrimidine
• 英文别名: 5'-fluorotoyocamycin；5'-deoxy-5'-fluorotoyocamycin；4-amino-7-[(2R,3R,4S,5S)-5-(fluoromethyl)-3,4-dihydroxyoxolan-2-yl]pyrrolo[2,3-d]pyrimidine-5-carbonitrile
• CAS: 155637-31-3
• 化学式: C₁₂H₁₂FN₅O₃
• 分子量: 293.257
• InChiKey: FAMWBNQLBODORX-WOUKDFQISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  130
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  4-amino-5-cyano-7-(5-deoxy-5-fluoro-β-D-ribofuranosyl)pyrrolo<2,3-d>pyrimidine 在 ammonium hydroxide 、 双氧水 作用下， 反应 3.0h， 以75%的产率得到5'-deoxy-5'-fluorosangivamycin
  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 2,3-di-O-benzoyl-5-deoxy-5-fluoro-β-D-ribofuranoside 在 palladium on activated charcoal 甲醇 、 三甲基氯硅烷 、 TMSTf 、 硫酸 、 氨 、 氢气 、 三乙胺 、 六甲基二硅氮烷 作用下， 以 1,4-二氧六环 、 溶剂黄146 为溶剂， 反应 89.0h， 生成 4-amino-5-cyano-7-(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

文献信息

• Synthesis of Primary Thioamides from Nitriles and Hydrogen Sulfide Catalyzed by Anion-Exchange Resin
  作者：Miroslav Bobek、Radek Liboska、Daniel Zyka

  DOI：10.1055/s-2002-33649

  日期：——

  A new method has been developed for converting nitriles into primary thioamides. Treatment of various nitriles (Table 1, entries 1-12) with gaseous hydrogen sulfide in a mixture of methanol-water or ethanol-water and in the presence of anion-exchange resin (Dowex I XX. SH form) at room temperature and ambient pressure gave the corresponding thioamides in 25-96% yield.

  已开发出一种将腈类转化为伯硫代酰胺的新方法。在室温和环境温度下，在存在阴离子交换树脂（Dowex I XX. SH 型）的情况下，在甲醇-水或乙醇-水的混合物中用气态硫化氢处理各种腈（表 1，条目 1-12）加压得到相应的硫代酰胺，产率为25-96%。