1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-4-methoxy thieno<3,2-d>pyrimidin-2-one | 153085-48-4

• 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-methoxy thieno<3,2-d>pyrimidin-2-one
• CAS: 153085-48-4
• 化学式: C₃₃H₂₆N₂O₉S
• 分子量: 626.643
• InChiKey: HMMPNCGFZVDPNE-GSTLAZBSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.67
• 重原子数：
  45.0
• 可旋转键数：
  9.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  132.25
• 氢给体数：
  0.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-4-methoxy thieno<3,2-d>pyrimidin-2-one 在 氨 作用下， 反应 14.0h， 以36%的产率得到4-methoxy-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：

  在 N-甲基咪唑 、 四氯化锡 、 三乙胺 、 三氯氧磷 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 34.5h， 生成 1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-4-methoxy 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