Efficient Transformation of Thymidine into 2′,3′-Didehydro-2′,3′-Dideoxy-Thymidine (D4T) Involving Opening of a 2,3′-Anhydro Derivative by Phenylselenol

Abstract

A new, high-yielding method for introduction of the selenophenyl residue at the 3′-position of thymidine is reported. This reaction avoided any strongly basic or reductive reagent, thus allowing the use of benzoate ester as a protective group at O-5′. Further oxidation-elimination sequence followed by basic deprotection afforded 2′,3′-didehydro-2′,3′-dideoxythymidine (D4T) in 67.5% overall yield from thymidine.