ON THE WAY TO GLYCOPROCESSING INHIBITORS - SYNTHESIS OF AN IMIDAZO-L-XYLO-PIPERIDINOSE DERIVATIVE

An eight-step synthetic sequence led from the known D-xylo-pentodialdo se 8 to imidazo-L-xylo-piperidinose 15, the key steps being the build- up of imidazole compound 12 by a van Leusen methodology and the intram olecular S(N)2 ring closure of the O-triflated benzylidene derivative 13. xylo-Piperidinose 15 appears in a half-chair conformation like the oxocarbonium ions which are the postulated intermediates in the glyco processing of the pyranose polysaccharides. This bicyclic azasugar sho uld be a glycosidase inhibitor.