2-((2R,3S)-5-Hydroxy-3-methoxy-tetrahydro-furan-2-ylmethoxy)-3H-pyrimidin-4-one | 1059105-77-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-((2R,3S)-5-Hydroxy-3-methoxy-tetrahydro-furan-2-ylmethoxy)-3H-pyrimidin-4-one
• 英文别名: 2-[[(2R,3S)-5-hydroxy-3-methoxyoxolan-2-yl]methoxy]-1H-pyrimidin-6-one
• CAS: 1059105-77-9
• 化学式: C₁₀H₁₄N₂O₅
• 分子量: 242.232
• InChiKey: HZNYWLHVRNDXJW-PMDVUHRTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  89.4
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-((2R,3S)-5-Hydroxy-3-methoxy-tetrahydro-furan-2-ylmethoxy)-3H-pyrimidin-4-one 在 吡啶 、 三氟甲磺酸三甲基硅酯 、 六甲基二硅氮烷 作用下， 以 氘代乙腈 为溶剂， 生成 2'-deoxy-3'-O-methyluridine
  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：

  3-Benzyloxymethyl-2-((2R,3S)-3-methoxy-2,3-dihydro-furan-2-ylmethoxy)-3H-pyrimidin-4-one 在 palladium dihydroxide sodium tetrahydroborate 、 mercury(II) diacetate 、 水 、 氢气 作用下， 生成 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

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.