Protecting group free glycosylation: one-pot stereocontrolled access to 1,2-<i>trans</i> glycosides and (1→6)-linked disaccharides of 2-acetamido sugars
Xin Qiu, Anna L. Garden, Antony J. Fairbanks
Abstract
Un-protected 2-acetamido sugars are stereoselectively converted into 1,2- trans glycosides and (1→6)-linked disaccharides without any protecting groups. Reaction proceeds via intermediate oxazolines which react with acceptors under acid catalysis.
Topics & Concepts
ChemistryGlycosideGlycosylYield (engineering)GlycosylationAqueous solutionProtecting groupSolventRegioselectivityArylStereoselectivityOrganic chemistryLeaving groupAlcoholAcceptorChlorideCatalysisAlkylBiochemistryCondensed matter physicsMaterials scienceMetallurgyPhysicsCarbohydrate Chemistry and SynthesisGlycosylation and Glycoproteins ResearchChemical Synthesis and Analysis