116457-68-2Relevant academic research and scientific papers
Synthesis of diphosphorylated and diphosphonylated Lipid A monosaccharide analogues via phosphite intermediates
Westerduin,Veeneman,van Boom
, p. 601 - 606 (2007/10/02)
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.
