A General Synthesis of 8,2′-Thioanhydropurine Nucleosides

Abstract

The synthesis of 8,2′-anhydro-8-mercapto-9-β-D-arabinofuranosyladenine,8,2′-anhydro-8-mercapto-9-β-D-arabinofuranosylguanine, and 8,2′-anhydro-8-mercapto-9-β-D-arabinofuranosylhypoxanthine is described. The anhydro ring is formed by simultaneous displacement of bromine from position-8 and carbonate from the 2′-position of the parent nucleoside using either sodium hydrogen sulfide or thiourea.