1-(2,5-di-O-acetyl-3-deoxy-β-D-erythro-pentofuranosyl)-4-(1,2,4-triazol-1-yl)-2(1H)-pyrimidone | 161109-95-1

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: 1-(2,5-di-O-acetyl-3-deoxy-β-D-erythro-pentofuranosyl)-4-(1,2,4-triazol-1-yl)-2(1H)-pyrimidone
• CAS: 161109-95-1
• 化学式: C₁₅H₁₇N₅O₆
• 分子量: 363.33
• InChiKey: BDEOFNYMRGELGF-OUCADQQQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.39
• 重原子数：
  26.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  127.43
• 氢给体数：
  0.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  1-(2,5-di-O-acetyl-3-deoxy-β-D-erythro-pentofuranosyl)-4-(1,2,4-triazol-1-yl)-2(1H)-pyrimidone 在 ammonium hydroxide 、 sodium ethanolate 作用下， 以 1,4-二氧六环 为溶剂， 反应 26.5h， 生成 3-脱氧胞苷
  参考文献：
  名称：

  Nucleosides. LVI¹Synthesis and Chemical Modifications of 3′-Deoxy-Pyrimidine Nucleosides

  摘要：

  3'-Deoxyuridine(1) and 3'-deoxycytidine(2) were prepared with improved yields by two different methods applying either the Barton procedure to appropriate 2',5'-di-O-protected pyrimidine nucleosides or by choosing the direct glycosylation of the pyrimidine bases with 1,2-di-O-acetyl-5-O-toluoyl-3-deoxy-D-erythro-pentofuranose via the silylation approach. Suitable protecting groups for the sugar moiety have been found in the trityl, tert-butyldimethylsilyl and the thexyl groups which are inert in the radical deoxygenation process. The newly synthesised compounds were characterised by elemental analyses and UV and H-1-NMR spectra.

  DOI：

  10.1080/15257779408012162
• 作为产物：
  描述：

  3-脱氧尿苷 在 吡啶 、 2-氯苯基二氯膦 作用下， 以 吡啶 为溶剂， 反应 68.0h， 生成 1-(2,5-di-O-acetyl-3-deoxy-β-D-erythro-pentofuranosyl)-4-(1,2,4-triazol-1-yl)-2(1H)-pyrimidone
  参考文献：
  名称：

  Nucleosides. LVI¹Synthesis and Chemical Modifications of 3′-Deoxy-Pyrimidine Nucleosides

  摘要：

  3'-Deoxyuridine(1) and 3'-deoxycytidine(2) were prepared with improved yields by two different methods applying either the Barton procedure to appropriate 2',5'-di-O-protected pyrimidine nucleosides or by choosing the direct glycosylation of the pyrimidine bases with 1,2-di-O-acetyl-5-O-toluoyl-3-deoxy-D-erythro-pentofuranose via the silylation approach. Suitable protecting groups for the sugar moiety have been found in the trityl, tert-butyldimethylsilyl and the thexyl groups which are inert in the radical deoxygenation process. The newly synthesised compounds were characterised by elemental analyses and UV and H-1-NMR spectra.

  DOI：

  10.1080/15257779408012162