Disaccharides to inositol saccharides: synthesis of α-D-galactopyranosyl-D-myo-inositol derivatives from a methyl 4-O-(α-D-galactopyranosyl)-α-D-glucopyranoside derivative

Abstract

The disaccharide derivative 3 has been transformed into the galactopyranosylcyclohexanone derivative 5 by means of Ferrier carbocycle reaction of the enosaccharide 4. Compound 5 was converted into the enone 6 and then into the allylic alcohol 7. Oxidation of compound 7 and the acetyl derivative 10 by OSO₄ gave the galactopyranosyl-D-myo-inositol derivatives 8 and 9, and 11 and 12, respectively, in good yields.