4-acetylamino-1-(3,4-diacetoxy-tetrahydro-furan-2-yl)-1H-pyrimidin-2-one | 63709-23-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-acetylamino-1-(3,4-diacetoxy-tetrahydro-furan-2-yl)-1H-pyrimidin-2-one
• CAS: 63709-23-9
• 化学式: C₁₄H₁₇N₃O₇
• 分子量: 339.305
• InChiKey: VYHDENBZWLJMOU-RAIGVLPGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.41
• 重原子数：
  24.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  125.82
• 氢给体数：
  1.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  4-acetylamino-1-(3,4-diacetoxy-tetrahydro-furan-2-yl)-1H-pyrimidin-2-one 在 氨 作用下， 以 甲醇 为溶剂， 反应 24.0h， 生成 1-(β-D-erytrhofuranosyl)cytidine
  参考文献：
  名称：

  (13C)-Substituted erythronucleosides: synthesis and conformational analysis by proton and carbon-13 NMR spectroscopy

  摘要：

  The erythronucleosides, 9-beta-D-erythrofuranosyladenine (1b), 1-beta-D-erythrofuranosylcytosine (2b), 9-beta-D-erythrofuranosylguanine (3b), and 1-beta-D-erythrofuranosyluracil (4b), were synthesized with and without C-13-substitution at C1' of the furanose ring. 75-MHz C-13 and 620-MHz H-1 NMR spectra of 1-4b were interpreted, in the latter case with the assistance of spectral simulation, and H-1-H-1, C-13-H-1, and C-13-C-13 spin couplings were used to assess furanose conformation. 3J(HH) data in (H2O)-H-2 were treated by computer to determine the preferred north and south conformers, their puckering amplitudes, and their mole fractions in solution, and J(CH) data were used to complement this analysis. A similar treatment of spin coupling data for the corresponding ribonucleosides 1-4a was also conducted to permit a comparison of furanose conformations in both series of compounds. Results show that the removal of the exocyclic hydroxymethyl group from 1-4a, giving 1-4b, significantly enhances the proportion of south conformers in aqueous ((H2O)-H-2) solution.

  DOI：

  10.1021/jo00032a032
• 作为产物：
  描述：

  N4-乙酰胞嘧啶 、 2,3,4-呋喃三醇,四氢-,三乙酸酯,(3R,4R)- 在 三氟甲磺酸三甲基硅酯 、 六甲基二硅氮烷 作用下， 生成 4-acetylamino-1-(3,4-diacetoxy-tetrahydro-furan-2-yl)-1H-pyrimidin-2-one
  参考文献：
  名称：

  (13C)-Substituted erythronucleosides: synthesis and conformational analysis by proton and carbon-13 NMR spectroscopy

  摘要：

  The erythronucleosides, 9-beta-D-erythrofuranosyladenine (1b), 1-beta-D-erythrofuranosylcytosine (2b), 9-beta-D-erythrofuranosylguanine (3b), and 1-beta-D-erythrofuranosyluracil (4b), were synthesized with and without C-13-substitution at C1' of the furanose ring. 75-MHz C-13 and 620-MHz H-1 NMR spectra of 1-4b were interpreted, in the latter case with the assistance of spectral simulation, and H-1-H-1, C-13-H-1, and C-13-C-13 spin couplings were used to assess furanose conformation. 3J(HH) data in (H2O)-H-2 were treated by computer to determine the preferred north and south conformers, their puckering amplitudes, and their mole fractions in solution, and J(CH) data were used to complement this analysis. A similar treatment of spin coupling data for the corresponding ribonucleosides 1-4a was also conducted to permit a comparison of furanose conformations in both series of compounds. Results show that the removal of the exocyclic hydroxymethyl group from 1-4a, giving 1-4b, significantly enhances the proportion of south conformers in aqueous ((H2O)-H-2) solution.

  DOI：

  10.1021/jo00032a032