5-O-benzyl 1-O-[[(2R,3S,5R)-5-(2,4-dioxo-5-thiophen-2-ylpyrimidin-1-yl)-3-hydroxyoxolan-2-yl]methyl] pentanedioate | 177779-38-3

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: 5-O-benzyl 1-O-[[(2R,3S,5R)-5-(2,4-dioxo-5-thiophen-2-ylpyrimidin-1-yl)-3-hydroxyoxolan-2-yl]methyl] pentanedioate
• CAS: 177779-38-3
• 化学式: C₂₅H₂₆N₂O₈S
• 分子量: 514.556
• InChiKey: JXCUQJCZFIYJKI-QKNQBKEWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.37
• 重原子数：
  36.0
• 可旋转键数：
  10.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  136.92
• 氢给体数：
  2.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  5-O-benzyl 1-O-[[(2R,3S,5R)-5-(2,4-dioxo-5-thiophen-2-ylpyrimidin-1-yl)-3-hydroxyoxolan-2-yl]methyl] pentanedioate 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 、 溶剂黄146 为溶剂， 反应 72.0h， 以12%的产率得到5-[[(2R,3S,5R)-5-[2,4-dioxo-5-(2-thienyl)pyrimidin-1-yl]-3-hydroxy-tetrahydrofuran-2-yl]methoxy]-5-oxo-pentanoic acid
  参考文献：
  名称：

  Synthesis of Mimics to Thymidine and 5-(2″-Thienyl)-2′-Deoxyuridine Triphosphates

  摘要：

  Dicarboxylic acid 5'-monoesters of thymidine and 5-(2-thienyl)-2 ''-deoxyuridine have been synthesised and evaluated as triphosphate mimics. Glutaric (25, 29), adipic (26, 30), pimelic (27, 31) and trans-1,4-cyclohexane dicarboxylic acids (28, 32) were employed to vary the distance between two carboxylate functions and were structurally compared to the triphosphate moiety by molecular modelling. The glutarate and adipate derivatives can assume conformations fitting the triphosphate, and the thienyl compounds 29 and 30 were the ones having overall best inhibitory activities against DNA pol alpha and HIV-1 RT.

  DOI：

  10.1080/07328319608002034
• 作为产物：
  描述：

  (2S)-2-氨基-5-(苄氧基)-5-氧代戊酸 在 sodium tetrahydroborate 、 草酰氯 作用下， 反应 144.25h， 生成 5-O-benzyl 1-O-[[(2R,3S,5R)-5-(2,4-dioxo-5-thiophen-2-ylpyrimidin-1-yl)-3-hydroxyoxolan-2-yl]methyl] pentanedioate
  参考文献：
  名称：

  Synthesis of Mimics to Thymidine and 5-(2″-Thienyl)-2′-Deoxyuridine Triphosphates

  摘要：

  Dicarboxylic acid 5'-monoesters of thymidine and 5-(2-thienyl)-2 ''-deoxyuridine have been synthesised and evaluated as triphosphate mimics. Glutaric (25, 29), adipic (26, 30), pimelic (27, 31) and trans-1,4-cyclohexane dicarboxylic acids (28, 32) were employed to vary the distance between two carboxylate functions and were structurally compared to the triphosphate moiety by molecular modelling. The glutarate and adipate derivatives can assume conformations fitting the triphosphate, and the thienyl compounds 29 and 30 were the ones having overall best inhibitory activities against DNA pol alpha and HIV-1 RT.

  DOI：

  10.1080/07328319608002034