title: FeCl3-promoted and ultrasound-assisted synthesis of resveratrol O-derived glycoside analogs.
abstract: Phenol derived O-glycosides were synthesized using a direct and convenient O-glycosidation, starting from acetylated sugars in the presence of FeCl3, an inexpensive, mild and benign Lewis acid catalyst. The reactions were carried out under both conventional and ultrasonic irradiation conditions. In general, improvement in rates and yields were observed when reactions were carried out under sonication compared with conventional conditions leading to the corresponding β-O-glycosides as the major anomer. Post-synthetic transformations of iodophenol intermediates led to new resveratrol O-glycoside analogs in good overall yields.
authors: Institut de Chimie de Nice UMR CNRS 7272, Université Nice-Sophia Antipolis, Parc Valrose, 06108 Nice Cedex 2, France; Laboratoire de Chimie des Plantes et de Synthèse Organique et Bioorganique, URAC23, Université Mohammed V-Agdal, Faculté des Sciences, B.P. 1014 Rabat, Morocco.
authors: Hamid
authors: H
authors: Marzag
authors: Centre Méditérranéen de Médecine Moléculaire UMR INSERM U1065, Equipe 2 Cell Death Differentiation and Cancer, Equipe Labellisée par la Ligue Nationale contre le Cancer, Université de Nice-Sophia Antipolis, C3M - Bâtiment ARCHIMED 151 route Saint Antoine de Ginestière, 06204 Nice, France.
authors: Guillaume
authors: G
authors: Robert
authors: Centre Méditérranéen de Médecine Moléculaire UMR INSERM U1065, Equipe 2 Cell Death Differentiation and Cancer, Equipe Labellisée par la Ligue Nationale contre le Cancer, Université de Nice-Sophia Antipolis, C3M - Bâtiment ARCHIMED 151 route Saint Antoine de Ginestière, 06204 Nice, France.
authors: Maeva
authors: M
authors: Dufies
authors: Laboratoire de Chimie des Plantes et de Synthèse Organique et Bioorganique, URAC23, Université Mohammed V-Agdal, Faculté des Sciences, B.P. 1014 Rabat, Morocco.
authors: Khalid
authors: K
authors: Bougrin
authors: Centre Méditérranéen de Médecine Moléculaire UMR INSERM U1065, Equipe 2 Cell Death Differentiation and Cancer, Equipe Labellisée par la Ligue Nationale contre le Cancer, Université de Nice-Sophia Antipolis, C3M - Bâtiment ARCHIMED 151 route Saint Antoine de Ginestière, 06204 Nice, France.
authors: Patrick
authors: P
authors: Auberger
authors: Institut de Chimie de Nice UMR CNRS 7272, Université Nice-Sophia Antipolis, Parc Valrose, 06108 Nice Cedex 2, France. Electronic address: benhida@unice.fr.
authors: Rachid
authors: R
authors: Benhida
mesh_terms: D002384:Catalysis; D060326:Chemistry Techniques, Synthetic; D002712:Chlorides / Q000737:chemistry*; D005290:Ferric Compounds / Q000737:chemistry*; D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry*; D010100:Oxygen / Q000737:chemistry*; D010165:Palladium / Q000737:chemistry; D000077185:Resveratrol; D013267:Stilbenes / Q000737:chemistry*; D014465:Ultrasonics
chemical_list: D002712:Chlorides; D005290:Ferric Compounds; D006027:Glycosides; D013267:Stilbenes; D010165:Palladium; D000077185:Resveratrol; D010100:Oxygen; C024555:ferric chloride
keywords: Iron catalysis; Resveratrol; Resveratrol O-glycosides; Ultrasound activation