Bioorganic & medicinal chemistry

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

C Crey-Desbiolles, M Kotera

Index: Crey-Desbiolles, Caroline; Kotera, Mitsuharu Bioorganic and Medicinal Chemistry, 2006 , vol. 14, # 6 p. 1935 - 1941

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Citation Number: 19

Abstract

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.