2-amino-9-[(2R,5S)-5-[[tert-butyl(dimethyl)silyl]oxymethyl]oxolan-2-yl]-3H-purin-6-one | 177779-53-2

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: 2-amino-9-[(2R,5S)-5-[[tert-butyl(dimethyl)silyl]oxymethyl]oxolan-2-yl]-3H-purin-6-one
• CAS: 177779-53-2
• 化学式: C₁₆H₂₇N₅O₃Si
• 分子量: 365.508
• InChiKey: MYEXKMLATXQCEB-WDEREUQCSA-N

物化性质

• 密度：
  1.32±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  25.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  108.05
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  2-amino-9-[(2R,5S)-5-[[tert-butyl(dimethyl)silyl]oxymethyl]oxolan-2-yl]-3H-purin-6-one 在 acetate buffer pH 4.5 、 溴 作用下， 反应 1.58h， 以24%的产率得到2-amino-8-bromo-9-[(2R,5S)-5-[[tert-butyl(dimethyl)silyl]oxymethyl]oxolan-2-yl]-1H-purin-6-one
  参考文献：
  名称：

  Synthesis and¹H and¹³C NMR Spectral Characteristics of 8-Bromo-2′,3′-Dideoxyguanosine and 8-Bromo-2′,3′-Dideoxyinosine¹

  摘要：

  Reaction of 2',3'-dideoxyguanosine 1a as 5'-O-tert-butyldimethylsilyl derivative Ib and 2',3'-dideoxyinosine 2a with bromine in acetate buffer conducted in heterogeneous medium afforded 8-bromo-2',3'-dideoxyguanosine 3a (44% after deprotection) and 8-bromo-2',3'-dideoxyinosine 4a (12%) respectively. The change of conformational preferences anti --> syn on 8-bromo substitution of 2',3'-dideoxynucleosides is reflected in the H-1 and C-13 NMR spectra by characteristic shifts of H-2', H-3', C-2' and C-3' signals.

  DOI：

  10.1080/07328319608002035
• 作为产物：
  描述：

  O-[(2R,3S,5R)-5-(2-amino-6-oxo-3H-purin-9-yl)-2-[[tert-butyl(dimethyl)silyl]oxymethyl]oxolan-3-yl] imidazole-1-carbothioate 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 1,4-二氧六环 为溶剂， 反应 1.0h， 以91%的产率得到2-amino-9-[(2R,5S)-5-[[tert-butyl(dimethyl)silyl]oxymethyl]oxolan-2-yl]-3H-purin-6-one
  参考文献：
  名称：

  Synthesis and¹H and¹³C NMR Spectral Characteristics of 8-Bromo-2′,3′-Dideoxyguanosine and 8-Bromo-2′,3′-Dideoxyinosine¹

  摘要：

  Reaction of 2',3'-dideoxyguanosine 1a as 5'-O-tert-butyldimethylsilyl derivative Ib and 2',3'-dideoxyinosine 2a with bromine in acetate buffer conducted in heterogeneous medium afforded 8-bromo-2',3'-dideoxyguanosine 3a (44% after deprotection) and 8-bromo-2',3'-dideoxyinosine 4a (12%) respectively. The change of conformational preferences anti --> syn on 8-bromo substitution of 2',3'-dideoxynucleosides is reflected in the H-1 and C-13 NMR spectra by characteristic shifts of H-2', H-3', C-2' and C-3' signals.

  DOI：

  10.1080/07328319608002035