CONFIGURATION OF GLYCOSIDIC LINKAGES IN OLIGOSACCHARIDES: IX. SYNTHESIS OF α- AND β-D-MANNOPYRANOSYL DISACCHARIDES
- 1 December 1961
- journal article
- research article
- Published by Canadian Science Publishing in Canadian Journal of Chemistry
- Vol. 39 (12), 2474-2485
- https://doi.org/10.1139/v61-327
Abstract
The Konigs-Knorr condensation of 4, 6-di-O-acetyl-2, 3-O-carbonyl-[alpha]-D-mannopyranosyl bromide with 1, 2, 3, 4-tetra-O-acetyl-[beta]-D-glucose provides a synthetic route to 6-O-[beta]-D-manno-pyranosyl-D-glucose. When some other derivatives of [alpha]-D-manno-pyranosyl bromide-the 2, 3, 4, 6-tetra-O-benzoyl-, 3,4,6-tri-O-acetyl, or 3,4, 6-tri-O-acetyl-2-O-benzyl derivative-are used as the halide component the -d-linked isomer of this disaccharide is produced. The steric outcome of Konigs-Knorr syntheses involving these and other derivatives of [alpha]-D-mannopyranosyl bromide is discussed in terms of the influence of neighboring groups, and of conformational and solvent effects. Lead tetraacetate oxidation of 6-O-[beta]-D-mannopyranosyl-D-glu-cose, followed by reduction, affords 4-O-[beta]-D-mannopyranosyl-D-eryth-ritol, a metabolite produced by Ustilago species (PRL 627).This publication has 9 references indexed in Scilit:
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