A simple and efficient method for synthesis of 5-substituted 2′-deoxyuridine nucleosides using metal–halogen exchange reaction of 5-iodo-2′-deoxyuridine sodium salt

Abstract

Treatment of the sodium salt of 2′-deoxy-3′, 5′-bis-O-(tert-butyldimethylsilyl)-5-iodouridine (3) with n-BuLi effected regioselective lithiation at the 5-position and the following reaction with various electrophiles afforded 5-substituted 2′-deoxyuridines including 1b, the precursor of stable spin-labeled 1a, in good yields.