6-Methyl-2-(methylthio)-4-pyrimidinol, TMS derivative

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 6-Methyl-2-(methylthio)-4-pyrimidinol, TMS derivative
• 英文别名: trimethyl-(6-methyl-2-methylsulfanylpyrimidin-4-yl)oxysilane
• 化学式: C₉H₁₆N₂OSSi
• 分子量: 228.39
• InChiKey: OTASQCGOBJBWCF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.72
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  60.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-Methyl-2-(methylthio)-4-pyrimidinol, TMS derivative 在 三氟甲磺酸三甲基硅酯 、 氨 、 间氯过氧苯甲酸 作用下， 以 甲醇 、 二氯甲烷 、 乙腈 为溶剂， 生成 6-甲基尿苷
  参考文献：
  名称：

  Stereoselective Synthesis of N1-6-Methyluridine and Related 2-Substituted Analogues

  摘要：

  Coupling reaction of 2-substituted-6-methyl-4(3H)-pyrimidinones (1a,b) with 1-O-acetyl-2,3,5-tri-O-benzoyl-beta-D-ribofuranose (ABR) afforded the corresponding N-1-2,6-disubstituted nucleosides (2a,b) without any trace of the N-3-isomer. The 2-methylthio-6-methyl derivative (2b) has then proved to be a key intermediate for the synthesis of N-1-6-methyluridine (4) and the corresponding N-1-2-amino-6-metyhl derivative (5), suggesting the possibility to obtain different 2,6-disubstituted derivatives by means of methylthio nucleophilic substitution. A successful solid phase application was also shown.

  DOI：

  10.3987/com-06-s(k)3
• 作为产物：
  描述：

  6-甲基-4-羟基-2-甲硫基嘧啶 、 六甲基二硅氮烷 在 硫酸氢铵 作用下， 生成 6-Methyl-2-(methylthio)-4-pyrimidinol, TMS derivative
  参考文献：
  名称：

  Stereoselective Synthesis of N1-6-Methyluridine and Related 2-Substituted Analogues

  摘要：

  Coupling reaction of 2-substituted-6-methyl-4(3H)-pyrimidinones (1a,b) with 1-O-acetyl-2,3,5-tri-O-benzoyl-beta-D-ribofuranose (ABR) afforded the corresponding N-1-2,6-disubstituted nucleosides (2a,b) without any trace of the N-3-isomer. The 2-methylthio-6-methyl derivative (2b) has then proved to be a key intermediate for the synthesis of N-1-6-methyluridine (4) and the corresponding N-1-2-amino-6-metyhl derivative (5), suggesting the possibility to obtain different 2,6-disubstituted derivatives by means of methylthio nucleophilic substitution. A successful solid phase application was also shown.

  DOI：

  10.3987/com-06-s(k)3