AuBr3 mediated glycosidations: synthesis of tetrasaccharide motif of the Leishmania donovani lipophosphoglycan

Abstract

Tetrasaccharide cap present in lipophosphoglycan of the Leishmania donovani responsible for visceral Leishmaniaisis is synthesized as a fully protected propargyl glycoside. AuBr3 mediated selective glycosylation of propargyl 1,2-orthoester in the presence of propargyl glycoside is employed as a key step to obtain propargyl containing oligomers. Further, propargyl tetrasaccharide is connected with a long chain hydrocarbon containing azidothiol functionality situated at two terminal ends via ‘click’ reaction.