Synthesis, NMR and X-ray studies on novel heteroaromatic aldoxime O-ether 2- and 2,3-unsaturated glycosides

[Display omitted] •Hydrolytically stable glycosidic bond was designed and performed between 2-deoxy sugars and heterocycles.•Heteroaromatic aldoxime O-ether 2- and 2,3-unsaturated glycosides were fully characterized by NMR and X-ray analysis.•Carbohydrate-derived oxime ethers were synthesized in good yields and high anomeric and E/Z selectivity. We present the synthesis of novel hydrolytically stable heteroaromatic oxime ether glycosides in very good yields and high anomeric selectivity. The products obtained are α-glycosides and the double bond configuration is E. The aldoxime O-ether carbohydrate derivatives were analysed by structural X-ray diffraction and NMR spectral data. A complete investigation on the glycoside structures, that includes conformation characteristics in the pyranose ring and heterocyclic alternative positions, is also described.