Efficient glycosylation with phenyl 2-azido-2-deoxy-1-seleno-α-d-galactosides of glycosyl acceptors with different reactivities has been developed. The reaction provided glycosides of 2-azido-2-deoxy-d-galactose in good to high yields. The stereochemical outcome of the glycosylation of reactive acceptors (3-trifluoroacetamidopropanol and methyl 2,3-O-isopropylidene-α-l-rhamnopyranoside) can be broadly varied from complete β- to high α-selectivity by changing the reaction solvent, promoter and protecting groups in the donor, while the glycosylation of less reactive allyl 2,2′,3,3′,6,6′-hexa-O-benzoyl-β-lactoside afforded the corresponding α-glycosides exclusively.