β-Selective xylulofuranosylation via a conformationally-restricted glycosyl donor

Abstract

Reported is the first stereoselective method for β-xylulofuranosylation, which employs 3,4-O-xylylene-protected thioglycoside donors. For most acceptors, the best results were observed with a donor (8) that possesses both the xylylene group and a benzoate ester at O-1. To demonstrate its utility, the methodology was applied to the first synthesis of the pentasaccharide repeating unit from the lipopolysaccharide O-antigen of Yersinia enterocolitica serovars O:5/O:5,27, a structure containing two β-xylulofuranose residues.