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Ionic liquids as phase transfer catalysts: Enhancing the biphasic extractive epoxidation reaction for the selective synthesis of β-O-glycosides

2017; Elsevier BV; Volume: 58; Issue: 38 Linguagem: Inglês

10.1016/j.tetlet.2017.08.033

1873-3581

Cintia C. Santiago, Leticia Lafuente, Rodolfo D. Bravo, Gisela Díaz, Agustı́n Ponzinibbio,

Organic and Inorganic Chemical Reactions

Ionic liquids promoted the direct epoxidation of glycals acting as PTC. 1,2-anhydrosugars were prepared by the oxidation of glycals under biphasic conditions with dimethydioxirane generated in situ from oxone/acetone and amphiphilic IL’s as catalysts. β-O-glycosides were synthesized in good yields by the nucleophilic ring opening of epoxy carbohydrate derivatives. Also, 3,4,6-benzyl protected carbohydrates and β-N-glycosides could be prepare by this method.