Synthesis of branched seven-membered 1-N-iminosugars and their evaluation as glycosidase inhibitors

Four branched tetra- and pentahydroxylated azepanes have been synthesized from a common azepane precursor through dihydroxylation followed by deoxygenation. They have been assayed as glycosidase inhibitors on a panel of 22 glycosidases and one methylated azepane displayed selective, competitive, and moderate inhibition toward bovine kidney alpha-L-fucosidase. (C) 2011 Elsevier Ltd. All rights reserved.