2'-deoxy-3',5'-di-O-(4-methylbenzoyl)inosine | 756494-13-0

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: 2'-deoxy-3',5'-di-O-(4-methylbenzoyl)inosine
• CAS: 756494-13-0
• 化学式: C₂₆H₂₄N₄O₆
• 分子量: 488.5
• InChiKey: VBBPCHGNDSZBNI-PWRODBHTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.11
• 重原子数：
  36.0
• 可旋转键数：
  6.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  125.4
• 氢给体数：
  1.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  2'-deoxy-3',5'-di-O-(4-methylbenzoyl)inosine 在 苄基三乙基氯化铵 、 N,N-二甲基苯胺 、 三氟乙酸 、 sodium iodide 、 三氯氧磷 作用下， 以 乙腈 、 丁酮 为溶剂， 反应 5.17h， 生成 9-[2-deoxy-3,5-di-O-(4-methylbenzoyl)-β-D-erythro-pentofuranosyl]-6-iodopurine
  参考文献：
  名称：

  S_NAr Iodination of 6-Chloropurine Nucleosides:  Aromatic Finkelstein Reactions at Temperatures Below −40 °C¹

  摘要：

  Mesitoyl or toluoyl esters of inosine and 2'-deoxyinosine were deoxychlorinated at C6 to give the crystalline 6-chloropurine nucleoside derivatives, which underwent quantitative conversion to the 6-iodo analogues with Nal/TFA/butanone at -50 to -40 degreesC. The 6-iodo compounds were efficient substrates for SNAr, Sonogashira, and Suzuki-Miyaura reactions, in contrast with the 6-chloro analogues, and gave good to high yields of C-N and C-C coupled products.

  DOI：

  10.1021/ol048987n
• 作为产物：
  描述：

  2'-脱氧肌苷 、 对甲基苯甲酰氯 在 吡啶 作用下， 反应 2.0h， 以87%的产率得到2'-deoxy-3',5'-di-O-(4-methylbenzoyl)inosine
  参考文献：
  名称：

  S_NAr Iodination of 6-Chloropurine Nucleosides:  Aromatic Finkelstein Reactions at Temperatures Below −40 °C¹

  摘要：

  Mesitoyl or toluoyl esters of inosine and 2'-deoxyinosine were deoxychlorinated at C6 to give the crystalline 6-chloropurine nucleoside derivatives, which underwent quantitative conversion to the 6-iodo analogues with Nal/TFA/butanone at -50 to -40 degreesC. The 6-iodo compounds were efficient substrates for SNAr, Sonogashira, and Suzuki-Miyaura reactions, in contrast with the 6-chloro analogues, and gave good to high yields of C-N and C-C coupled products.

  DOI：

  10.1021/ol048987n