Catherine AlexSatsawat VisansirikulAlexei V. DemchenkoUniversity of Missouri-St. LouisMahidol University2020-10-052020-10-052020-09-14Organic and Biomolecular Chemistry. Vol.18, No.34 (2020), 6682-6695147705202-s2.0-85090250795https://repository.li.mahidol.ac.th/handle/20.500.14594/58955© The Royal Society of Chemistry. O-Picoloyl protecting groups at remote positions can affect the stereoselectivity of glycosylation by means of the H-bond-mediated aglycone delivery (HAD) pathway. A new practical method for the stereoselective synthesis of β-glycosides of mannosamine is reported. The presence of the O-picoloyl group at the C-3 position of a mannosamine donor can provide high or complete stereocontrol. The method was also utilized for the synthesis of a biologically relevant trisaccharide related to the capsular polysaccharide of Streptococcus pneumoniae serotype 4. Also reported herein is a method to achieve complete α-manno stereoselectivity with mannosamine donors equipped with 3-O-benzoyl group. This journal isMahidol UniversityBiochemistry, Genetics and Molecular BiologyChemistryArticleSCOPUS10.1039/d0ob01640c