Stereoselectivity in radical reactions of 2′-deoxynucleosides. A synthesis of an isostere of 3′-azido-3′-deoxythymidine-5′-monophosphate (AZT-5′ monophosphate)

Abstract The bulky t-butyldiphenylsilyl group, attached to the 3′-hydroxyl of the uronic acid from thymidine, permits a stereoselective formation of a carbon-carbon bond using the 4′ carbon radical. Taking advantage of this stereoselectivity an isostere of 3′-azido-3′-deoxythymidine-5′-monophosphate (AZT 5′-monophosphate) has been synthesised.