Photoactivable deoxyadenosine mimic, 3-deaza-3-nitro-2′-deoxyadenosine (2), was prepared using two different synthetic routes. The first route involved base catalyzed glycosylation of 3-deaza-3-nitroadenine, which was prepared by regioselective nitration of 3- deazaadenine. In the second route, the convertible nucleoside 6-O-(2, 4, 6-trimethylphenyl)- 3-deaza-2′-deoxyadenosine (28) was used to introduce 6-NH2 group in the last step.