A CONVENIENT METHOD FOR THE SYNTHESIS AND RANEY NICKEL DESULFURIZATION OF 5′-DEOXY-5′ -M ETHYLTHIOADENOSINE

Abstract

Abstract A convenient procedure for the preparation of 5′-deoxy-5′-methylthioadenosine is reported. Chlorination of adenosine with thionyl chloride yielded 5′-chloro-5′-deoxyadenosine. Reaction of 5′-chloro-5′-deoxyadenosine with aqueous methylmercaptide anion yielded 5′-deoxy-5′-methylthioadenosine. Hydrogenolysis of 5′-deoxy-5′-methylthioadenosine over Raney nickel in water produced 5′-deoxyadenosine. This procedure affords a high yield of readily purified 5′-deoxyadenosine while avoiding the use of anhydrous solvents and pyrophoric reagents. The procedure illustrates the utility of sulfur reagents to accomplish high value added transformations in nucleoside chemistry.