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  • Title: Fluoronucleosides, isothiocyanato C-nucleosides, and thioureylene di-C-nucleosides via cyclic sulfates.
    Author: Fuentes J, Angulo M, Pradera MA.
    Journal: J Org Chem; 2002 Apr 19; 67(8):2577-87. PubMed ID: 11950304.
    Abstract:
    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.
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