9-β-D-(1'-13C)erythrofuranosyladenine | 138722-89-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: 9-β-D-(1'-13C)erythrofuranosyladenine
• 英文别名: (2R,3R,4R)-2-(6-aminopurin-9-yl)(213C)oxolane-3,4-diol
• CAS: 138722-89-1
• 化学式: C₉H₁₁N₅O₃
• 分子量: 238.207
• InChiKey: DTGVOXMKTYPSSO-BMNVDSNYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.34
• 重原子数：
  17.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  119.31
• 氢给体数：
  3.0
• 氢受体数：
  8.0

反应信息

• 作为产物：
  描述：

  N6-苯甲酰基腺嘌呤 在 三氟甲磺酸三甲基硅酯 、 氨 、 六甲基二硅氮烷 作用下， 以 甲醇 为溶剂， 反应 37.0h， 生成 9-β-D-(1'-13C)erythrofuranosyladenine
  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