Palmitoyl diol S- and O-phosphoroamidates of some sterols

Abstract

The hexamethylphosphorus triamide activated by the addition of iodine at the optimum molar ratio 1.05:0.05 was used as a phosphorylating reagent to synthesize 1-palmitoyloxyethyl-2-O-, 1-palmitoyloxypropyl-3-O- and 1-palmitoyloxybutyl-4-O-(N,N-dimethylamido)thiophosphate and -phosphate derivatives of beta-sitosterol, cholesterol and stigmasterol in a one-pot procedure with overall yields of 80-87%. 1-Palmitoyloxypropyl-3-O-(cholesteryl-3-O)-(N,N-dimethylamido++ +) phosphite was used as a model synthon for the preparation of transamidated morpholido-thiophosphate and -phosphate analogues with final yields of 82-86%.