Facile syntheses of 2-chloro- and 2-tosyloxy-2’-deoxyinosine as their tert-butyldimethylsilyl ethers are delineated. Diazotization-chlorination of protected O⁶-allyl-2’-deoxyguanosine, obtained in three steps from 2’-deoxyguanosine, followed by deallylation yielded 2-chloro-2’-deoxyinosine. A protected O⁶-benzyl 2'-deoxyguanosine derivative was converted to the O⁶-benzyl-2’-deoxyxanthosine analogue. This was easily transformed into the 2-tosyloxy derivative, which upon catalytic debenzylation gave the 2-tosyloxy-2’-deoxyinosine. Both electrophilic nucleosides were used for the preparation of N-substituted 2’-deoxyguanosine analogues via displacement of the leaving groups. A 2-step, 1-pot conversion of O⁶-allyl-2-chloro-2’-deoxyguanosine to the final modified 2’-deoxyinosine derivatives was also feasible. Overall yields from this two-step procedure compared very favorably with the yields from the displacement reactions.