Cleavage of the C–C linkage between the sugar and the aglycon in C-glycosylphloroacetophenone, and the NMR spectral characteristics of the resulting di-C-glycosyl compound Original Research Article

The treatment of unprotected mono-C-β-d-glucopyranosylphloroacetophenone with a cation-exchange resin in anhydrous acetonitrile afforded both a phloroacetophenone and a di-C-β-d-glucopyranosylphloroacetophenone. Treatment of an unprotected mono-C-(2-deoxy-β-d-arabino-hexopyranosyl)phloroacetophenone (mono-C-2-deoxy-β-d-glucopyranosylphloroacetophenone) also afforded both the aglycon and di-C-(2-deoxy-β-d-arabino-hexopyranosyl)phloroacetophenone. The reaction mixtures were acetylated, and the structures of the isolated products were determined by NMR spectroscopy. This is the first demonstration of the formation of a di-C-glycosyl compound during the chemical cleavage of the C–C linkage between the sugar and the aglycon in an aryl C-glycosyl derivative.