On the Way to Glycoprocessing Inhibitors. Synthesis of an imidazo‐L‐xylo‐piperidinose derivative

Abstract

AbstractAn eight‐step synthetic sequence led from the known D‐xylo‐pentodialdose 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 intramolecular SN2 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 glycoprocessing of the pyranose polysaccharides. This bicyclic azasugar should be a glycosidase inhibitor.