3',5'-O-phosphonoalkylidene derivatives of 1-(2-deoxy-β-D-threo- pentofuranosyl)thymine: Synthesis and reactivity

Article abstract of DOI:10.1016/S0040-4020(98)00654-1

Various 3',5'-O-(1-phosphonoalkylidene) derivatives of 1-(2-deoxy-β-D- threo-pentofuranosyl)thymine bearing a substituent in the ω-position of the alkylidene chain were prepared by the redox reaction of diethyl chlorophosphite with six-membered 3',5'-orthoesters of xylo-dT. Susceptibility of ω-haloalkylidene derivatives for nucleophilic substitution is discussed. The configuration of the final phosphonates was determined by 2D-ROESY NMR experiments.