Silatranyl-nucleosides: transition state analogues for phosphoryl transfer reactions

A novel class of compounds that contain a silatrane moiety attached to or incorporated within a nucleoside is described. These compounds are transition state analogues for phosphoryl transfer reactions and as such have potential antiviral and anticancer properties. The two-step synthesis of 3′-O-(trimethyl)silatranylthymidine (1) in 17% yield is reported. The aqueous half-life of 1 was determined to be 62 h by 1H NMR. The syntheses of three 2′,3′-protected-5′-O-silatranyladenosines in 25–55% yields are also described.