1-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)thieno<3,2-d>pyrimidine-2,4-dione | 153085-43-9

• 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-acetyl-β-D-ribofuranosyl)thieno<3,2-d>pyrimidine-2,4-dione
• CAS: 153085-43-9
• 化学式: C₁₇H₁₈N₂O₉S
• 分子量: 426.404
• InChiKey: NCDMGIJBGKIRBV-BRXULGCHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.08
• 重原子数：
  29.0
• 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：
  142.99
• 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-acetyl-β-D-ribofuranosyl)thieno<3,2-d>pyrimidine-2,4-dione 在 ammonium hydroxide 作用下， 生成 4-amino-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-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)thieno<3,2-d>pyrimidine-2,4-dione 在 吡啶 、 氨 作用下， 以 甲醇 为溶剂， 反应 96.0h， 生成 1-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)thieno<3,2-d>pyrimidine-2,4-dione
  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