Synthesis, NMR and X-ray studies on novel heteroaromatic aldoxime O-ether 2- and 2, 3-unsaturated glycosides. Issue 35 (27th August 2020)

• Record Type: Journal Article
• Authors: Lafuente, Leticia; Rojas, Agustín H.; Piro, Oscar E.; Echeverría, Gustavo A.; Ponzinibbio, Agustín
• Is Part Of: Tetrahedron letters. Volume 61:Issue 35(2020)
• Publication Date: 2020-08-27
• Subjects: Oxime ether glycosides -- Heteroaromatic Schiff Base -- 0H5 conformation -- X-ray diffraction; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2020.152241
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: 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. Abstract: 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.