SYNTHESIS OF SOME DISACCHARIDES CONTAINING PENT-2-ENO-PYRANOSE RESIDUES

Article abstract of DOI:10.1016/S0008-6215(00)85314-8

Two methods of linking racemic 2,3-dideoxypent-2-enopyranos-4-ulose to suitably protected monosaccharide derivatives have been evaluated.The resulting diastereoisomeric mixtures containing D-glucose, D-galactose, and L-rhamnose derivatives in the "aglycon" part were fractionated, and configurations were assigned to ten disaccharide precursors.Disaccharides containing non-reducing 2,3-dideoxy-α-D- and α-L-pent-2-enopyranose residues and their satureted analogues have been obtained by lithium aluminum hydride reduction of selected pentosylulose-monosaccharides.Inversion of configuration at the allylic position (C-4) in some unsatureted disaccharides is also described.