SYNTHESIS OF OLIGOSACCHARIDES OF L-FUCOSE CONTAINING α- AND β-ANOMERIC CONFIGURATIONS IN THE SAME MOLECULE

Article abstract of DOI:10.1016/0008-6215(83)84046-4

Some L-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-O-p-nitrobenzoyl-α-L-fucopyranosyl bromide gave α-L-fucopyranosides stereospecifically, but 2,3,4-tri-O-acetyl-α-L-fucopyranosyl bromide gave mixtures with selectivity favouring the β anomer.A tetrasaccharide was prepared containing both α- and β-L-fucopyranosyl residues in the same molecule, as part of a structure occuring in some extracellular bacterial polysaccharides.The configuration and positions of substitution of fucopyranosyl residues were clearly shown by 1H- and 13C-n.m.r. data.