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Synthesis of oligosaccharides of l-fucose containing α- and β-anomeric configurations in the same molecule

✍ Scribed by Harold M. Flowers

Publisher: Elsevier Science
Year: 1983
Tongue: English
Weight: 687 KB
Volume: 119
Category: Article
ISSN: 0008-6215
DOI: 10.1016/0008-6215(83)84046-4

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✦ Synopsis

ARSTRACI Some I,-fucopyranosyl di-, tri-, and tetra-saccharides containing D-glUCOSe and D-galactose have been synthesised. The use of mercuric cyanide and 2-O-benzyl-3,4-di-0-p-nitrobenzoyl-L-u-L-fucopyranosyl bromide gave cY-t_-fucopyranosides stereospecifically, but 2,3,4-tri-0-acetyl-a-t_-fucopyranosyl bromide gave mixtures with selectivity favouring the /3 anomer. A tetrasaccharide was prepared containing both (Y-and P-r.-fucopyranosyl residues in the same molecule, as part of a structure occurring in some extracellular bacterial polysaccharides. The configuration and positions of substitution of fucopyranosyl residues were clearly shown by 'H-and "C-n.m.r.

data.

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