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. © 2001 Elsevier Science Ltd.
Ponticelli, F., Trendafilova, A., Valoti, M., Saponara, S., Sgaragli, G.P. (2001). Synthesis and antiperoxidant activity of new phenolic O-glycosides. CARBOHYDRATE RESEARCH, 330(4), 459-468 [10.1016/S0008-6215(00)00313-X].
Synthesis and antiperoxidant activity of new phenolic O-glycosides
Ponticelli, Fabio;Valoti, Massimo;Saponara, Simona;Sgaragli, Gian Pietro
2001-01-01
Abstract
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. © 2001 Elsevier Science Ltd.
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https://hdl.handle.net/11365/19008
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