4-amino-5-cyano-7-(5-azido-5-deoxy-β-D-ribofuranosyl)pyrrolo<2,3-d>pyrimidine | 155637-30-2

• 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-azido-5-deoxy-β-D-ribofuranosyl)pyrrolo<2,3-d>pyrimidine
• 英文别名: 4-amino-7-[(2R,3R,4S,5R)-5-(azidomethyl)-3,4-dihydroxyoxolan-2-yl]pyrrolo[2,3-d]pyrimidine-5-carbonitrile
• CAS: 155637-30-2
• 化学式: C₁₂H₁₂N₈O₃
• 分子量: 316.279
• InChiKey: DKIVYRQEUFTPFD-WOUKDFQISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  145
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  4-amino-5-cyano-7-(5-azido-5-deoxy-β-D-ribofuranosyl)pyrrolo<2,3-d>pyrimidine 在 ammonium hydroxide 、 双氧水 作用下， 以78%的产率得到4-amino-5-carboxamido-7-(5-azido-5-deoxy-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：

  4-氨基-5-氰基-7-(beta-d-呋喃核糖)吡咯并[2,3-d]嘧啶 在 sodium azide 、 四溴化碳 、 三苯基膦 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以40%的产率得到4-amino-5-cyano-7-(5-azido-5-deoxy-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 5′-Fluoro-5′-deoxy-and 5′-Amino-5′-Deoxytoyocamycin and Sangivamycin and Some Related Derivatives
  作者：Moheshwar Sharma、Yi X. Li、Miroslav Ledvina、Miroslav Bobek

  DOI：10.1080/15257779508010707

  日期：1995.11

  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.