Action of nucleophiles on 2,3′-anhydrothymidine: side-reactions involving the possible intermediacy of 2,5′-anhydro-1-(2-deoxy- [formula omitted]- [formula omitted]- Threo-pentofuranosyl) thymine

Abstract

2,3′-Anhydrothymidine ( 1 ) reacts with the sodium salt of propane-2-thiol and with sodium phenyl selenide to give 5′-substituted products [( 3b ) and ( 3c ), respectively] in addition to the expected 3′-substituted 2′,3′-dideoxynucleoside derivatives [( 2b ) and ( 2c )].