Catherine AlexSatsawat VisansirikulAlexei V. DemchenkoUniversity of Missouri-St. LouisMahidol University2022-08-042022-08-042021-03-28Organic and Biomolecular Chemistry. Vol.19, No.12 (2021), 2731-2743147705202-s2.0-85103508277https://repository.li.mahidol.ac.th/handle/20.500.14594/76242Reported herein is a new method for a highly effective synthesis of β-glycosides from mannuronic acid donors equipped with the 3-O-picoloyl group. The stereocontrol of glycosylations was achieved by means of the H-bond-mediated aglycone delivery (HAD). The method was utilized for the synthesis of a tetrasaccharide linkedviaβ-(1 → 3)-mannuronic linkages. We have also investigated 3,6-lactonized glycosyl donors that provided moderate to high β-manno stereoselectivity in glycosylations. A method to achieve complete α-manno stereoselectivity with mannuronic acid donors equipped with 3-O-benzoyl group is also reported.Mahidol UniversityBiochemistry, Genetics and Molecular BiologyChemistryArticleSCOPUS10.1039/d1ob00188d