Silyl phosphite and ylide reagents to the synthesis of methylene analogs of natural polyphosphates

Luis A Vargas

Abstract

 Methylene polyphosphate nucleosides are desired analogs used to investigate the role of phosphate transfer in biological systems. They may also elucidate the mechanisms of enzymatic reactions that utilize natural nucleoside polyphosphates as substrates. The synthesis of these analogs has been restricted by the lack of a method to introduce a phosphinate group containing a versatile functional group for further synthetic elaboration. We describe here the synthesis of two reagents: Bis (trimethylsilyl} trimethylsilyloxymethyl phosphinite and Phenyl (Chloromethyl} [(triphenylphosphoranylidene}-methyl}] phosphinate chloride, both of which contain versatile groups needed for the complete synthesis of methylene polyphosphate nucleosides.