2-(methylthio)-3-(benzyloxymethyl)pyrimidin-4-one | 146202-39-3

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 2-(methylthio)-3-(benzyloxymethyl)pyrimidin-4-one
• 英文别名: 2-Methylsulfanyl-3-(phenylmethoxymethyl)pyrimidin-4-one
• CAS: 146202-39-3
• 化学式: C₁₃H₁₄N₂O₂S
• 分子量: 262.332
• InChiKey: PPMXTBPQMSGILH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  67.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(methylthio)-3-(benzyloxymethyl)pyrimidin-4-one 在 sodium tetrahydroborate 、 mercury(II) diacetate 、 水 、 potassium hydride 作用下， 生成 3-Benzyloxymethyl-2-((2R,3S)-5-hydroxy-3-methoxy-tetrahydro-furan-2-ylmethoxy)-3H-pyrimidin-4-one
  参考文献：
  名称：

  New approach to the synthesis of .beta.-2'-deoxyribonucleosides: intramolecular Vorbrueggen coupling

  摘要：

  Silylation of the O2,5'-linked nucleoside 7 followed by treatment with trimethylsilyl triflate affords the O2,5-anhydro nucleoside 9 and its hydrolysis product the beta-anomer of the 2-deoxyuridine 10 in good yield in the first example of an oxygen-bridged intramolecular Vorbruggen coupling.

  DOI：

  10.1021/jo00056a004
• 作为产物：
  描述：

  2-甲硫基-4-嘧啶酮 、 苄基氯甲基醚 在 双(三甲基硅烷基)氨基钾 作用下， 以70%的产率得到2-(methylthio)-3-(benzyloxymethyl)pyrimidin-4-one
  参考文献：
  名称：

  New approach to the synthesis of .beta.-2'-deoxyribonucleosides: intramolecular Vorbrueggen coupling

  摘要：

  Silylation of the O2,5'-linked nucleoside 7 followed by treatment with trimethylsilyl triflate affords the O2,5-anhydro nucleoside 9 and its hydrolysis product the beta-anomer of the 2-deoxyuridine 10 in good yield in the first example of an oxygen-bridged intramolecular Vorbruggen coupling.

  DOI：

  10.1021/jo00056a004

文献信息

• New approach to the synthesis of .beta.-2'-deoxyribonucleosides: intramolecular Vorbrueggen coupling
  作者：Michael E. Jung、Claire Castro

  DOI：10.1021/jo00056a004

  日期：1993.2

  Silylation of the O2,5'-linked nucleoside 7 followed by treatment with trimethylsilyl triflate affords the O2,5-anhydro nucleoside 9 and its hydrolysis product the beta-anomer of the 2-deoxyuridine 10 in good yield in the first example of an oxygen-bridged intramolecular Vorbruggen coupling.