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ChemInform Abstract

Key step in the title synthesis is the cycloaddition of imines, in situ generated from D-erythrose derivatives like (I) and aniline derivative (II), with the ketene derived from mesyloxyacetyl chloride (III). Transformation of the so obtained mesyloxy-substituted β-lactam (IV) to the azide (V) provides access to a number of further modifications, e.g. formation of the trifluoroacetylamino derivative (VII) or N-dearylation to compound (VIII). Aminolysis and carbamoylation of derivative (VIII) affords the hitherto unknown diamino-dideoxy-D-mannonamide (XV). None of the newly synthesized compounds, obtained by debenzylation of compounds (VII), (XI), and (XIII), possesses inhibitory activity against sialidases isolated from various viruses and bacteria.