The Synthesis of 3-O-(beta-D-Glucopyranosyl)-and 3-O-(beta-Laminaribiosyl)-isofagomines,Potent Inhibitors of a 1,3-beta-D-Glucan

摘要

The glycosylation of 4,6-0-benzylidene-N-benzyloxycarbonylisofagomine with a D-glucosyl and a laminari-biosyl trichloroacetimidate has given,after removal of protecting groups,3-O-(beta-D-glucopyranosyl)-and 3-O-(beta-laminaribiosyl)-isofagomines.Also included are similar glycosylations of a related tetrahydrooxazine.3-O-(beta-D-Glucopyranosyl)-and 3-O-(beta-laminaribiosyl)-isofagomines acted as potent inhibitors of a barley l,3-beta-D-glucan endo-hydrolase,with ID_50 values of 7.8 and 3.1 muM,respectively.