Toward Synthesis of the Isosteric Sulfonate Analogues of the AT-III Binding Domain of Heparin

D-Glucuronate and L-Iduronate containing disaccharides related to the antithrombin-binding pentasaccharide of heparin, in which one of the sulfate esters is systematically replaced by a sodium sulfonatomethyl moiety, were synthesized. The sulfonic acid group was Introduced by stereoselective radical addition onto the exomethylene moiety of the appropriate glycoside derivatives, and the resulting sulfonatomethyl glucosides; were used as acceptors.