1-(2-deoxy-3,5-di-O,O-(4-methylbenzoyl)-α-D-ribofuranosyl)-2-[methyl(phenyl)amino]-1H-pyrimidin-4-one | 1033942-78-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-(2-deoxy-3,5-di-O,O-(4-methylbenzoyl)-α-D-ribofuranosyl)-2-[methyl(phenyl)amino]-1H-pyrimidin-4-one
• CAS: 1033942-78-7
• 化学式: C₃₂H₃₁N₃O₆
• 分子量: 553.615
• InChiKey: SYSHQIRONHBDTF-GKRYNVPLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.0
• 重原子数：
  41.0
• 可旋转键数：
  8.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  99.96
• 氢给体数：
  0.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  1-(2-deoxy-3,5-di-O,O-(4-methylbenzoyl)-α-D-ribofuranosyl)-2-[methyl(phenyl)amino]-1H-pyrimidin-4-one 在 氨 作用下， 以 甲醇 为溶剂， 反应 16.0h， 以93%的产率得到1-(2-deoxy-α-D-ribofuranosyl)-2-[methyl(phenyl)amino]-1H-pyrimidin-4-one
  参考文献：
  名称：

  Synthesis of N 2-Arylisocytidines and N 2-Aryl-2′-deoxyisocytidines

  摘要：

  2-(Arylamino)pyrimidin-4-ones were synthesized, silylated, and condensed with l,2,3,5-tetra-O-acetyl-beta-D-ribofuranoside to afford the corresponding N-2-aryl protected isocytidines. Deprotection of the acetylated isocytidines using saturated NH3 in MeOH solution gave 1-(beta-D-ribofuranosyl)-2-(arylamino)-4-pyrimidinones. Methyl 2-deoxy-3,5-di-O-toluyl-alpha/beta-D-ribofuranoside was prepared and condensed with the previously silylated bases to afford the anomeric mixture of protected nucleosides. The pure beta-anomers were synthesized with better yield by treating the sodium salts of N-2-arylisocytosine derivatives with 2-deoxy-3,5-di-O-toluyl-alpha-D-ribofuranosyl chloride. Deprotection of the latter anomers afforded the corresponding free hydroxyl derivatives. The synthesized free nucleosides are under antiviral and oligonucleotide investigations.

  DOI：

  10.1007/s00706-007-0671-9
• 作为产物：
  描述：

  N-甲基苯胺 在 ammonium sulfate 、 六甲基二硅氮烷 作用下， 以 溶剂黄146 为溶剂， 反应 10.0h， 生成 1-(2-deoxy-3,5-di-O,O-(4-methylbenzoyl)-α-D-ribofuranosyl)-2-[methyl(phenyl)amino]-1H-pyrimidin-4-one
  参考文献：
  名称：

  Synthesis of N 2-Arylisocytidines and N 2-Aryl-2′-deoxyisocytidines

  摘要：

  2-(Arylamino)pyrimidin-4-ones were synthesized, silylated, and condensed with l,2,3,5-tetra-O-acetyl-beta-D-ribofuranoside to afford the corresponding N-2-aryl protected isocytidines. Deprotection of the acetylated isocytidines using saturated NH3 in MeOH solution gave 1-(beta-D-ribofuranosyl)-2-(arylamino)-4-pyrimidinones. Methyl 2-deoxy-3,5-di-O-toluyl-alpha/beta-D-ribofuranoside was prepared and condensed with the previously silylated bases to afford the anomeric mixture of protected nucleosides. The pure beta-anomers were synthesized with better yield by treating the sodium salts of N-2-arylisocytosine derivatives with 2-deoxy-3,5-di-O-toluyl-alpha-D-ribofuranosyl chloride. Deprotection of the latter anomers afforded the corresponding free hydroxyl derivatives. The synthesized free nucleosides are under antiviral and oligonucleotide investigations.

  DOI：

  10.1007/s00706-007-0671-9