Graphical Abstract: The reaction of (+)-D-glucose with 4-chloroaniline or 3,5-dibromoaniline leads almost exclusively to the β-configuration of glucosylated anilines. The acetylating of 2-(3,5-dibromophenylamino)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol is less selective than in case of the 2-(4-chlorophenylamino)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol.