| Abstract | Using acid catalysed reaction of 1,6:3,4-dianhydro-2-O-p-toluenesulfonyl-beta-D-galactopyranose (I) with mono-, di-, tri- and tetraethylene glycol, 4-O-oligoethylene glycol derivatives of 1,6-anhydro-2-O-p-toluenesulfonyl-beta-D-glucopyranose II-V were obtained which were converted to 4-O-substituted 1,6:2,3-dianhydro-beta-D-mannopyranoses VI-IX under the effect of sodium hydroxide. Of them 4-O-(2-hydroxyethyl)- and 4-O-(11-hydroxy-3,6,9-trioxaundecyl) derivatives VI and IX were intramolecularly cyclized in basic medium under formation of 1,6-anhydro-3,4-O-ethylene-B-D-altropyranose (X) or 1,6-anhydro-2,4-O-(3,6,9-trioxaundecane-1,11-diyl)-beta-D-glucopyranose (XV), respectively. Oxidation of the hydroxyl group in compound XV led to corresponding 3-ulose XIX, the reduction of which with sodium borohydride gave an isomer of compound XV, i.e. compound XX of D-allo-configuration. The structures of the compounds described in this paper were proved using H-1 and C-13 NMR spectra. Compounds XV, XIX and XX represent a new structural type of sugar crown-ethers. |
