1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-4-thioxo thieno<3,2-d>pyrimidin-2-one | 153085-46-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-4-thioxo thieno<3,2-d>pyrimidin-2-one
• CAS: 153085-46-2
• 化学式: C₃₂H₂₄N₂O₈S₂
• 分子量: 628.683
• InChiKey: BCXAFRSAIYPEHT-PAHOUZJPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.33
• 重原子数：
  44.0
• 可旋转键数：
  8.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  125.92
• 氢给体数：
  1.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-4-thioxo thieno<3,2-d>pyrimidin-2-one 在 氨 、 potassium carbonate 作用下， 以 四氢呋喃 为溶剂， 反应 19.0h， 生成 4-S-methyl-1-(β-D-ribofuranosyl)thieno<3,2-d>pyrimidin-2-one
  参考文献：
  名称：

  Synthesis of 1-(β-D-Ribofuranosyl)Thieno[3,2-d] Pyrimidine-2,4-Dione and 4-Substituted Derivatives

  摘要：

  Regiospecific ribosylation of the bis(trimethylsilyl) derivative of thieno[3,2-d]pyrimidine-2,4-dione in the presence of a Lewis acid followed by debenzoylation has afforded 1-(beta-D-ribofuranosyl)thieno[3,2-d]pyrimidine-2,4-dione, a uridine analogue. The site of ribosylation and anomeric configuration of this N-nucleoside were established by NMR and UV. Thiation of the beta-anomer was followed by treatment with methanolic ammonia to afford 4-amino-1-(beta-D-ribofuranosyl)thieno [3,2-d]pyrimidin-2-one, a cytidine analogue.

  DOI：

  10.1080/07328319308018567
• 作为产物：
  描述：

  1,3-二氢噻吩[3,2-D]嘧啶-2,4-二酮 在 劳森试剂 、 ammonium sulfate 、 四氯化锡 作用下， 以 1,2-二氯乙烷 、 甲苯 为溶剂， 反应 47.0h， 生成 1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-4-thioxo thieno<3,2-d>pyrimidin-2-one
  参考文献：
  名称：

  Synthesis of 1-(β-D-Ribofuranosyl)Thieno[3,2-d] Pyrimidine-2,4-Dione and 4-Substituted Derivatives

  摘要：

  Regiospecific ribosylation of the bis(trimethylsilyl) derivative of thieno[3,2-d]pyrimidine-2,4-dione in the presence of a Lewis acid followed by debenzoylation has afforded 1-(beta-D-ribofuranosyl)thieno[3,2-d]pyrimidine-2,4-dione, a uridine analogue. The site of ribosylation and anomeric configuration of this N-nucleoside were established by NMR and UV. Thiation of the beta-anomer was followed by treatment with methanolic ammonia to afford 4-amino-1-(beta-D-ribofuranosyl)thieno [3,2-d]pyrimidin-2-one, a cytidine analogue.

  DOI：

  10.1080/07328319308018567