The synthesis of 2,3-didehydro-2,4-dideoxy-4-guanidinyl-N- acetylneuraminic acid: A potent influenza virus sialidase inhibitor

Article abstract of DOI:10.1016/0008-6215(94)84065-2

The synthesis of a number of 5-acetamido-2,6-anhydro-3,5-dideoxy-D-galacto-non-2-enonic acid (Neu5Ac2en, 1) analogues has received considerable attention over the past decade. We have recently reported the design and biological evaluation of 5-acetamido-4-amino-2,6-anhydro-3,4,5-trideoxy-D-glucero-D-galacto-no n-2- enonic acid (4-amino-Neu5Ac2en, 2) and 5-acetomido-2,6-anhydro-4-guanidino- 3,4,5-trideoxy-D-glycero-D-galacto-non-2-enonic acid (4-guanidino-Neu5Ac2en, 3) as influenza virus sialidase inhibitors. The synthetic strategy that we adopted for the preparation of 3 required the introduction of nitrogen at C-4 of 1.