2',3',5'-tri-O-(4-methylbenzoyl)inosine | 756494-12-9

• 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',3',5'-tri-O-(4-methylbenzoyl)inosine
• 英文别名: [(2R,3R,4R,5R)-3,4-bis[(4-methylbenzoyl)oxy]-5-(6-oxo-1H-purin-9-yl)oxolan-2-yl]methyl 4-methylbenzoate
• CAS: 756494-12-9
• 化学式: C₃₄H₃₀N₄O₈
• 分子量: 622.634
• InChiKey: GCGMBRQBRLQAFP-QWOIFIOOSA-N

物化性质

• 熔点：
  210-213 °C(Solvent: Ethanol)
• 沸点：
  833.4±75.0 °C(Predicted)
• 密度：
  1.39±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 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：
  147
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  2',3',5'-tri-O-(4-methylbenzoyl)inosine 在 苄基三乙基氯化铵 、 N,N-二甲基苯胺 、 三氯氧磷 作用下， 以 乙腈 为溶剂， 反应 0.17h， 以85%的产率得到6-chloro-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 、 肌苷 在 吡啶 作用下， 反应 2.0h， 以89%的产率得到2',3',5'-tri-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

文献信息

• Selective Removal of the 2‘- and 3‘-<i>O</i>-Acyl Groups from 2‘,3‘,5‘-Tri-<i>O</i>-acylribonucleoside Derivatives with Lithium Trifluoroethoxide¹
  作者：Ireneusz Nowak、Carl T. Jones、Morris J. Robins

  DOI：10.1021/jo0600104

  日期：2006.4.1

  Selective cleavage of O2' and O3' ester groups from ribonucleoside derivatives has been accomplished with Dowex 1 x 2 (CF3CH2O-) in 2,2,2-trifluoroethanol (TFE) or lithium trifluoroethoxide/TFE. Deacylations with Li+ -OCH2CF3/TFE proceed at ambient temperature (or with mild heating) to give the 5'-O-acyl derivatives in superior yields and higher purity than prior approaches for selective O2' and O3' ester deprotection.
• S_NAr Iodination of 6-Chloropurine Nucleosides:  Aromatic Finkelstein Reactions at Temperatures Below −40 °C¹
  作者：Jiangqiong Liu、Zlatko Janeba、Morris J. Robins

  DOI：10.1021/ol048987n

  日期：2004.8.1

  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.