2-Amino-9-[(2R,3R,4R,5R)-3,4-bis-(tert-butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-5-hydroxy-5,7-dihydro-9H-purine-6,8-dione | 832729-60-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-Amino-9-[(2R,3R,4R,5R)-3,4-bis-(tert-butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-5-hydroxy-5,7-dihydro-9H-purine-6,8-dione
• CAS: 832729-60-9
• 化学式: C₂₈H₅₅N₅O₇Si₃
• 分子量: 658.03
• InChiKey: GRRIIKWKXNWWFN-NXACTXNWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.48
• 重原子数：
  43.0
• 可旋转键数：
  8.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  157.3
• 氢给体数：
  3.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  2-Amino-9-[(2R,3R,4R,5R)-3,4-bis-(tert-butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-5-hydroxy-5,7-dihydro-9H-purine-6,8-dione 以 丙酮 为溶剂， 反应 2.0h， 生成 1-[(2R,3R,4R,5R)-3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-7-imino-1,3,6,8-tetraaza-spiro[4.4]nonane-2,4,9-trione
  参考文献：
  名称：

  Characterization of 5-Hydroxy-8-oxo-7,8-dihydroguanosine in the Photosensitized Oxidation of 8-Oxo-7,8-dihydroguanosine and Its Rearrangement to Spiroiminodihydantoin

  摘要：

  The photosensitized oxidation of 2',3',5'-tris-(O-tert-butyldimethylsilyl)-8-oxo-7,8-dihydroguansine (8-oxoG) with singlet oxygen was studied by low-temperature NMR. A stable intermediate was characterized at -60 degreesC by C-13, 2D NMR HMBC spectra, and chemical shifts calculated by hybrid Hallree-Fock density functional theory which agreed with the structure 5-hydroperoxy-8-oxo-7,8-dihydroquanosine. Reduction of this intermediate at low temperature afforded the corresponding alcohol, the long-postulated 5-hydroxy8-oxo-7,8-dihydroguanosine, the last intermediate in the formation of spiroiminodihydantoin. Upon warming to room temperature, this alcohol rearranges to form the spiroiminodihydantoin in good yield within 2 h.

  DOI：

  10.1021/ja030678p
• 作为产物：
  描述：

  2-Amino-9-[(2R,3R,4R,5R)-3,4-bis-(tert-butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-5-hydroperoxy-5,7-dihydro-9H-purine-6,8-dione 在 二甲基硫 作用下， 以 丙酮 为溶剂， 生成 2-Amino-9-[(2R,3R,4R,5R)-3,4-bis-(tert-butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-5-hydroxy-5,7-dihydro-9H-purine-6,8-dione
  参考文献：
  名称：

  Characterization of 5-Hydroxy-8-oxo-7,8-dihydroguanosine in the Photosensitized Oxidation of 8-Oxo-7,8-dihydroguanosine and Its Rearrangement to Spiroiminodihydantoin

  摘要：

  The photosensitized oxidation of 2',3',5'-tris-(O-tert-butyldimethylsilyl)-8-oxo-7,8-dihydroguansine (8-oxoG) with singlet oxygen was studied by low-temperature NMR. A stable intermediate was characterized at -60 degreesC by C-13, 2D NMR HMBC spectra, and chemical shifts calculated by hybrid Hallree-Fock density functional theory which agreed with the structure 5-hydroperoxy-8-oxo-7,8-dihydroquanosine. Reduction of this intermediate at low temperature afforded the corresponding alcohol, the long-postulated 5-hydroxy8-oxo-7,8-dihydroguanosine, the last intermediate in the formation of spiroiminodihydantoin. Upon warming to room temperature, this alcohol rearranges to form the spiroiminodihydantoin in good yield within 2 h.

  DOI：

  10.1021/ja030678p