Lysek, RobertFavre, SylvainVogel, Pierre2012-07-042012-07-042012-07-04200710.1016/j.tet.2007.03.149https://infoscience.epfl.ch/handle/20.500.14299/83510WOS:000252081800021Starting from (+/-)-7-oxanorbornenone ((+/-)-14), (+/-)-(1RS, 2RS, 3SR, 6SR)-6-azidocyclohex-4-en-1,2,3-triol ((+/-)-24) and (+/-)- 1RS, 2RS, 3SR, 6RS)-6-azidocyclohex-4-en-1,2,3-triol ((+/-)-26) were obtained. Epoxidation of the latter cyclohexene derivative gave two epoxides (+/-)-30 and (+/-)-31 that were converted into (+/-)-conduramine F-1 epoxides (+/-)-10 and (epoxides (+/-)-30 and (+/-)-31 that were converted into (+/-)-conduramine F-1 epoxides (+/-)-10 and (+/-)-11 and N-substituted derivatives (+/-)-12 and (+/-)-13. Compound (+/-)-(1RS, 2SR, 3RS, 4SR, 5RS, 6SR)-5-({[4-(trifluoromethyl) phenyl] methyl} amino)-7-oxabicyclo[4.1.0]heptane-2,3,4- triol ((+/-)-12c) is a good, non-competitive inhibitor of beta-xylosidase from Aspergillus niger (K-i=2.2 mu M), and (+/-)( 1RS, 2RS, 3SR, 4RS, 5SR, 6SR)-5-{[(biphenyl-4-yl) methyl] amino}-7-oxabicyclo[4.1.0] heptane-2,3,4-triol ((+/-)-13d) is a good inhibitor of alpha-glucosidase from brewer's yeast (Ki 2.8 mu M, non-competitive). (c) 2007 Elsevier Ltd. All rights reserved.Alpha-Glucosidase InhibitorsLysosomal Storage DisordersType-2 Diabetes-MellitusDerivatives Naked SugarsN-Linked GlycosylationHepatitis-B-VirusNeuraminidase InhibitorEndoplasmic-ReticulumInfluenza-VirusOseltamivir Phosphatetext::conference output::conference proceedings::conference paper