A SIMPLE ONE POT SYNTHESIS OF AROMATIC STEROIDAL AND NONSTEROIDAL C-GLUCOSIDES VIA O-GLUCOSIDES

Treatment of 2,3,4,6-tetra-O-benzyl-beta-D-glucopyranosyl trifluoroacetate with an appropriate aromatic steroid under acid catalysis afforded first the O-glucopyranosides which subsequently rearranged to the corresponding C-glucopyranosides, useful for the synthesis of 2-beta-D-glucopyranosyl-3-hydroxy-1,3,5(10)-estratrien-17-one (1), or of 2-beta-D-glucopyranosyl-1,3,5(10)-estratriene-3,17beta-diol (2). The general applicability of the route was demonstrated by the synthesis of 1-beta-D-glucopyranosylnaphth-2-ol (3) and 2-beta-D-glucopyranosylnaphth-1-ol (4). Optimal conditions for regeneration of the hydroxy groups of the glucopyranosyl ring was also described. Unambiguous determination of the structure of all new compounds was obtained by means of H-1-NMR spectra at 500 MHz.