PMID: 11330889May 2, 2001Paper

Chemical synthesis of linear and cyclic unnatural oligosaccharides by iterative glycosidation of ketoses

Chemistry : a European Journal
A DondoniV Bertolasi

Abstract

The development of an efficient method for the stereoselective synthesis of alpha-D-(2-->1)-linked ketoside oligomers is described. The method is based on an iterative protocol composed of two key steps: a) the coupling of a thiazolylketosyl phosphite donor with an hydroxymethylketoside acceptor; and b) the introduction of the hydroxy-methyl group at the anomeric carbon atom of the resulting oligomer. To highlight its efficiency, the protocol was used in the assembly of D-galacto-2-heptulopyranose-containing oligoketosides through alpha-(2-->1) linkages up to the pentameric stage. The yield of the isolated oligomers ranged from 48 % in the first cycle to 29% in the fourth cycle. Having employed a pentenyl-substituted hydroxymethylketoside acceptor in the first cycle, all the derived oligomers contained the pentenyl group at their reducing end. This group was exploited to transform the linear oligomers into cyclic products through intramolecular glycosidation. The major product derived from the linear trisaccharide was confirmed by X-ray crystallography to be the cyclotris-(2-->1)-(alpha-D-galacto-2-heptulopyranosyl). The structure of this compound was essentially that of a [9]crown-3 ether bearing three galactopyranose rings sp...Continue Reading

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Citations

Feb 19, 2013·Chemistry : a European Journal·Mélissa Boultadakis-ArapinisThomas Lecourt
Jun 17, 2006·Chemical Communications : Chem Comm·Patricia BalbuenaJosé M García Fernández
Sep 17, 2008·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·M Isabel García-MorenoJosé M García Fernández
May 20, 2009·Chemical Reviews·Sarah Van der Jeught, Christian V Stevens
May 26, 2010·Chemical Reviews·Alessandro Dondoni, Alberto Marra
Oct 22, 2010·Journal of the American Chemical Society·Mélissa Boultadakis-ArapinisThomas Lecourt
Mar 13, 2015·Organic Letters·Paresh M Vadhadiya, Chepuri V Ramana
May 13, 2004·Chemical Reviews·Alessandro Dondoni, Alberto Marra

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