6-iodo-9-[2,3,5-tri-O-(4-methylbenzoyl)-β-D-ribofuranosyl]purine | 756494-15-2

• 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: 6-iodo-9-[2,3,5-tri-O-(4-methylbenzoyl)-β-D-ribofuranosyl]purine
• 英文别名: [(2R,3R,4R,5R)-5-(6-iodopurin-9-yl)-3,4-bis[(4-methylbenzoyl)oxy]oxolan-2-yl]methyl 4-methylbenzoate
• CAS: 756494-15-2
• 化学式: C₃₄H₂₉IN₄O₇
• 分子量: 732.531
• InChiKey: MQDUYOPLKJKGRA-QWOIFIOOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  46
• 可旋转键数：
  11
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  132
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  1-己炔 、 6-iodo-9-[2,3,5-tri-O-(4-methylbenzoyl)-β-D-ribofuranosyl]purine 在 copper(l) iodide 、 四(三苯基膦)钯 三乙胺 作用下， 反应 0.33h， 以92%的产率得到6-(hexyn-1-yl)-9-[2,3,5-tri-O-(4-methylbenzoyl)-β-D-ribofuranosyl]purine
  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：

  对甲基苯甲酰氯 在 吡啶 、 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 7.17h， 生成 6-iodo-9-[2,3,5-tri-O-(4-methylbenzoyl)-β-D-ribofuranosyl]purine
  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