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Full Paper
Stereoselective Dihydroxylation Reaction of Alkenyl β-D-Hexopyranosides: A Methodology for the Synthesis of Glycosylglycerol Derivatives and 1-O-Acyl-3-O-β-D-glycosyl-sn-glycerol Analogues
Article first published online: 29 DEC 2011
DOI: 10.1002/ejoc.201101539
Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Additional Information
How to Cite
Vega-Pérez, J. M., Palo-Nieto, C., Periñán, I., Vega-Holm, M., Calderón-Montaño, J. M., López-Lázaro, M. and Iglesias-Guerra, F. (2012), Stereoselective Dihydroxylation Reaction of Alkenyl β-D-Hexopyranosides: A Methodology for the Synthesis of Glycosylglycerol Derivatives and 1-O-Acyl-3-O-β-D-glycosyl-sn-glycerol Analogues. Eur. J. Org. Chem., 2012: 1237–1252. doi: 10.1002/ejoc.201101539
Publication History
- Issue published online: 13 FEB 2012
- Article first published online: 29 DEC 2011
- Manuscript Received: 20 OCT 2011
Funded by
- Junta de Andalucía
- Spanish Ministerio de Educación y Ciencia
- Fondos Europeos para el Desarrollo Regional. Grant Numbers: P06-FQM-01885, CTQ2007-61185
- Ministerio de Asuntos Exteriores y Cooperación. Grant Number: A/023577/09
Keywords:
- Synthetic methods;
- Asymmetric synthesis;
- Carbohydrates;
- Diastereoselectivity;
- Biological activity;
- Dihydroxylation
Abstract
A variety of new glycosylglycerol derivatives have been prepared by stereoselective dihydroxylation of a range of alkenyl β-D-hexopyanosides under Donohoe's conditions. We have studied the relationship between the diastereoisomeric excess and the structural features of the precursor (sugar and alkenyl moieties). The stereochemical yields demonstrated that the presence of a hydrogen-bond donor group (OH, NHAc) at the 2-position of the sugar moiety is required to obtain high levels of stereofacial discrimination. New 1-O-acyl-3-O-β-D-glycosyl-sn-glycerol analogues were obtained by functionalisation of the primary hydroxy group with a fatty acid. Preliminary cytotoxic activity assays of both glycosylglycerol and glycoglycerolipid analogues are also presented.