Abstract Reaction of 2′, 3′-dideoxyguanosine 1a as 5′-O-tert-butyldimethylsilyl derivative 1b and 2′, 3′-dideoxyinosine 2a with bromine in acetate buffer conducted in heterogeneous medium afforded 8-bromo-2′, 3′-dideoxyguanosine 3a (44% after deprotection) and 8-bromo-2′, 3′-dideoxyinosine 4a (12%) respectively. The change of conformational preferences anti→ syn on 8-bromo substitution of 2′, 3′- ...