Synthesis of (E)-5-[2-(Tri-n-butylstannyl)vinyl] Substituted 2′-Deoxyuridine Derivatives for Use in Halogenation and Radiohalogenation Reactions

Abstract

A facile synthesis is reported for 5-[2-(tri-n-butyl-stannyl)vinyl]-2′-deoxyuridine 1, starting from commercial 5-iodo-2′-deoxyuridine 2 via the stannylation reaction as the key step. The 3′,5′-di-O-acetyl-N(3)-p-toluoyl-protected analog of 1, compound 9, was then prepared. Electrophilic fluorination of 9 with carrier-added [18F]F2 provided the desired (E) and (Z) fluorovinyl compounds 10, but not as the major products. The E/Z ratio of 10 was 2 : 1. The main product of the reaction was the proton substituted compound 11.