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Ultrason Sonochem. 2015 Jan;22:15-21. doi: 10.1016/j.ultsonch.2014.05.022. Epub 2014 Jun 10.

FeCl3-promoted and ultrasound-assisted synthesis of resveratrol O-derived glycoside analogs.

Author information

1
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.
2
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.
3
Laboratoire de Chimie des Plantes et de Synthèse Organique et Bioorganique, URAC23, Université Mohammed V-Agdal, Faculté des Sciences, B.P. 1014 Rabat, Morocco.
4
Institut de Chimie de Nice UMR CNRS 7272, Université Nice-Sophia Antipolis, Parc Valrose, 06108 Nice Cedex 2, France. Electronic address: benhida@unice.fr.

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.

KEYWORDS:

Iron catalysis; Resveratrol; Resveratrol O-glycosides; Ultrasound activation

PMID:
24961448
DOI:
10.1016/j.ultsonch.2014.05.022
[Indexed for MEDLINE]
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