Convergent synthesis of the pentasaccharide repeating unit of the biofilms produced by Klebsiella pneumoniae (Beilstein Journal of Organic Chemistry)

Abstract A pentasaccharide repeating unit containing α-linked D-glucuronic acid, β-linked D-mannose, corresponding to the repeating unit of biofilms produced by Klebsiella pneumoniae, has been synthesized using a stereoselective [2 + 3] convergent glycosylation strategy. The β-D-mannosidic moiety has been synthesized using a D-mannose-derived thioglycoside by a two-step activation process. Late stage TEMPO-mediated oxidation of the pentasaccharide derivative using phase-transfer reaction conditions furnished the target compound in satisfactory yield. Beilstein J. Org. Chem. 2019, 15, 431–436. doi:10.3762/bjoc.15.37