Synthesis and antiperoxidant activity of new phenolic O-glycosides Original Research Article

We describe the synthesis of some 3-tert-butyl-4-hydroxyphenyl d-glycopyranosides by reaction of tert-butylhydroquinone with β-d-pentaacetyl-glucose, β-d-pentaacetyl-galactose, 2-acetamido- and 3,4,6-tri-O-acetyl-2-butanamido-2-deoxy-β-d-glucopyranosyl chlorides as well as the formation of anomeric 3-tert-butyl-4-hydroxyphenyl 4,6-di-O-acetyl-2,3-dideoxy-d-erythro-hex-2-eno-pyranosides by reaction between tert-butylhydroquinone and 3,4,6-tri-O-acetyl-d-glucal. All compounds, except 3-tert-butyl-4-hydroxyphenyl α- and β-d-glucopyranosides, inhibited lipid peroxidation with a degree of potency comparable to that of tert-butyl hydroxyanisole.