Efficient synthesis of monophosphoryl lipid A mimetic RC-529

An efficient approach for the facile synthesis of a potent vaccine adjuvant RC-529 is described. The synthetic strategy relies on flexible use orthogonal protecting groups, which makes it possible to accomplish selective phosphorylation, glycosylation and acylation, respectively. In addition, readily cleaved 2-naphthylmethyl (Nap) ether allyl esters as permanent groups greatly facilitates final global deprotection steps obtain pure RC-529. This work will contribute lipid A its derivatives.