SmI 2-mediated reactions of diethyl iodomethylphosphonate with esters and lactones: a highly stereoselective synthesis of a precursor of the C-glycosyl analogue of thymidine 5′-(β- l-rhamnosyl)diphosphate

Abstract

In the presence of samarium iodide diethyl iodomethylphosphonate reacts with esters to afford β-ketophosphonates. The protocol has been applied to sugar lactones to afford in fairly good yields intermediates that are useful precursors for a variety of potentially bioactive compounds, such as the C-glycosyl analogue of thymidine 5′-(β- l-rhamnosyl)diphosphate.