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

PIRO, OSCAR E.; LAFUENTE, LETICIA; ECHEVERRÍA, GUSTAVO A.; ROJAS, AGUSTÍN H.; PONZINIBBIO, AGUSTÍN

TETRAHEDRON LETTERS

PERGAMON-ELSEVIER SCIENCE LTD

Lugar: Amsterdam; Año: 2020 vol. 61

0040-4039

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.