Synthesis of 3-deaza-3-nitro-2′-deoxyadenosine

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.

Deoxyadenosine mimicking photoactivable nitro nucleoside, 3-deaza-3-nitro-2′-deoxyadenosine, was synthesized.Figure optionsDownload as PowerPoint slide