Imidazole-1-carbothioic acid O-[(2R,3S,5R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-(6-oxo-1,6-dihydro-purin-9-yl)-tetrahydro-furan-3-yl] ester | 177779-54-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: Imidazole-1-carbothioic acid O-[(2R,3S,5R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-(6-oxo-1,6-dihydro-purin-9-yl)-tetrahydro-furan-3-yl] ester
• 英文别名: O-[(2R,3S,5R)-2-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-5-(6-oxo-3H-purin-9-yl)oxolan-3-yl] imidazole-1-carbothioate
• CAS: 177779-54-3
• 化学式: C₃₅H₃₂N₆O₆S
• 分子量: 664.742
• InChiKey: GFFWHOTURIZKPP-FRXPANAUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.85
• 重原子数：
  48.0
• 可旋转键数：
  10.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  127.54
• 氢给体数：
  1.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  Imidazole-1-carbothioic acid O-[(2R,3S,5R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-(6-oxo-1,6-dihydro-purin-9-yl)-tetrahydro-furan-3-yl] ester 在 偶氮二异丁腈 、 三正丁基氢锡 、 溶剂黄146 作用下， 以 1,4-二氧六环 为溶剂， 反应 2.5h， 生成 2',3'-二脱氧肌苷
  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：

  2'-脱氧肌苷 以 吡啶 、 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 生成 Imidazole-1-carbothioic acid O-[(2R,3S,5R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-(6-oxo-1,6-dihydro-purin-9-yl)-tetrahydro-furan-3-yl] ester
  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