Conformational behavior of peracetylated β-d-mannopyranosyl methanesulfonamide: implications for the mechanism of sulfonamidoglycosylation of carbohydrate derivatives

► Conformational behavior of the glycosyl sulfonamide has been investigated from a theoretical and experimental point of view. ► Conformations were analyzed in terms of exo- and endo-anomeric effects and steric factors. ► An explanation of the stereochemical outcome of sulfonamidoglycosylations was given.