An alternative high yielding and highly stereoselective method for preparing an alpha-Neu5NAc-(2,6)-D-GalN3 building block suitable for further glycosylation |
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Authors: | Laurent Nicolas Lafont Dominique Boullanger Paul Mallet Jean Maurice |
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Affiliation: | Laboratoire de Chimie Organique II-Glycochimie, Unité Mixte de Recherche CNRS 5181, Université Lyon 1, Chimie Physique Electronique de Lyon, 43 Boulevard du 11 Novembre 1918, F-69622 Villeurbanne, France. |
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Abstract: | This paper deals with new approaches to alpha-Neu5NAc-(2,6)-D-GalN3 building blocks, suitable as glycosylation donors. The major improvement, by comparison with the results of the literature, lies in the glycosylation step of a new d-galactosamine acceptor (tert-butyldimethylsilyl 3-O-acetyl-2-azido-2-deoxy-beta-D-galactopyranoside) with O-methyl-S-[methyl(5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-alpha-D-galacto-non-2-ulopyranosyl)onate] dithiocarbonate as the N-acetylneuraminic acid donor. The reaction affords the expected disaccharide in high yield (85%) and a complete alpha-Neu5NAc stereoselectivity. A subsequent oxidation step, eliminating the glycal by-product allows an easier purification. Afterwards, the tert-butyldimethylsilyl disaccharide can be transformed into a donor, after cleavage of the anomeric group in smooth conditions. |
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Keywords: | smallcaps" >d-Galactosamine N-Acetylneuraminic acid α-Glycosylation Glycal oxidation |
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