Synthesis of O2,2′-cyclo-β-D-arabinofuranosyl- and β-D-arabinofuranosyl-5-fluorocytosine

Article abstract of DOI:10.1007/BF00526095

Methods for the synthesis of 5-fluorocytosine by direct fluorination of cytidine tetraacetate with elementary fluorine in acetic acid and by amination of 5-fluorouridine triacetate by the action of sodium hydride and p-toluenesulfonyl chloride and subsequent ammonolysis were studied. 5-Fluorocytidine was converted to O², 2′-cyclo-β-D-arabinofuranosyl-5-fluorocytosine by the successive action of acetylsalicylyl chloride and acetyl chloride in methanol to remove the protective groups. Removal of the protective groups by means of a methanol solution of ammonia gave β-D-arabinofuranosyl-5-fluorocytosine. The latter was also obtained by amination of β-D-arabinofuranosyl-5-fluorouracil tribenzoate.