Synthesis and influenza virus sialidase inhibitory activity of the 5-desacetamido analogue of 2,3-didehydro-2,4-dideoxy-4-guanidinyl-N-acetylneuraminic acid (GG167)

Abstract

The title compound 2b has been synthesised in 8 steps from 2-deoxy-D-glucose (2-DG). Key transformations were an aldolase reaction utilising 2-DG to form the 9 carbon sugar 3, and then introduction of the required unsaturation and a 4-amino substitutent in a one-pot process. The poor inhibitory activity of 2b demonstrates that the 5-acetamido substitutent in 2,3-didehydro-2,4-dideoxy-4-guanidinyl-N-acetylneuraminic acid (GG167) 1 is critical for sialidase binding.