Fluoronucleosides, isothiocyanato C-nucleosides, and thioureylene di-C-nucleosides via cyclic sulfates.
Cyclic sulfates of N- and C-nucleosides (D-ribo and D-erythro configurations, respectively) are used to prepare 3'-fluoro and 3'-azido D-xylo N-nucleosides and L-threo C-nucleosides. The reduction of the 3'-azido C-nucleosides (furan, imidazoline-2-thione, and pyrrole derivatives) gives 3'-amino C-nucleosides, which, by reaction with thiocarbonyldiimidazole, are transformed into 3'-isothiocyanato C-nucleosides. Reaction of the 3'-amino with the 3'-isothiocyanato C-nucleosides gives thioureylene di-C-nucleosides, a type of nucleotide analogue with a nonionic bridge isosteric of the phosphate group.
Fuentes
José
J
Departamento de Química Orgánica, Facultad de Química, Universidad de Sevilla, E-41071 Seville, Spain. jfuentes@cica.es
Angulo
Manuel
M
Pradera
M Angeles
MA
D001386:Azides / Q000737:chemistry; D002625:Chemistry, Organic / Q000379:methods; D002855:Chromatography, Thin Layer; D003500:Cyclization; D006845:Hydrocarbons, Fluorinated / Q000737:chemistry; D017879:Isothiocyanates / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D015394:Molecular Structure; D009705:Nucleosides / Q000138:chemical synthesis / Q000737:chemistry; D013055:Spectrophotometry, Infrared; D017550:Spectroscopy, Fourier Transform Infrared; D013237:Stereoisomerism; D013431:Sulfates / Q000737:chemistry*; D013872:Thionucleosides / Q000737:chemistry
D001386:Azides; D006845:Hydrocarbons, Fluorinated; D017879:Isothiocyanates; D009705:Nucleosides; D013431:Sulfates; D013872:Thionucleosides