Synthesis of diphosphorylated and diphosphonylated Lipid A monosaccharide analogues via phosphite intermediates

Article abstract of DOI:10.1002/recl.19871061201

The synthesis of two Lipid A monosaccharide analogues, 3-O-palmitoyl-2-deoxy-2-palmitamido-α-d-glucopyranose 1,4-diphosphate (1) and the corresponding 1,4-bis(1H-phosphonate) (2), is described. The introduction of the phosphate functions was achieved via phosphitylation of the anomeric and non-anomeric hydroxyl groups with the monofunctional phosphitylating reagents benzyl 2-cyanoethyl N,N-diethylphosphoramidite (9) and salicyl phosphochloridite (10). Oxidation of the intermediate phosphite triester and subsequent removal of all the protective groups afforded the target molecules 1 and 2.