Selection of Neighboring Group Participation Intermediates of Fully Acylated Donors around the Glycosylation Sites in Oligosaccharide Acceptors

Abstract

Stereo-and regio-selective formation of glycosidic linkages are a challenging topic in oligosaccharide syntheses. The stereoselective construction of 1,2-trans-glycosides generally involves neighboring group participation, which is less successful when synthesizing -1,3-linked oligosaccharides. The combined steric effect of a 2-O-substituent and an aglycon moiety in acceptors increases the efficiency of glycosylation via neighboring group participation. This steric effect was reduced by using vicinal polyol acceptors and was demonstrated in the synthesis of 1,3-linked branched oligosaccharides. ASSOCIATED CONTENT Supporting InformationThe Supporting Information is available free of charge on the ACS Publications website at DOI: Detailed experimental procedures, characterization, and 1 H and 13 C spectra of new compounds The Supporting Information is available free of charge on the ACS Publications website. brief description (file type, i.e., PDF) brief description (file type, i.e., PDF)