SYNTHESIS OF THE POTENT INFLUENZA NEURAMINIDASE INHIBITOR 4-GUANIDINO NEU5AC2EN - X-RAY MOLECULAR-STRUCTURE OF 5-ACETAMIDO-4-AMINO-2,6-ANHYDRO-3,4,5-TRIDEOXY-D-ERYTHRO-L-GLUCO-NONONIC ACID

An efficient and high-yielding synthesis of 4-guanidino Neu5Ac2en, the potent anti-influenza A and B compound, is described. The route exploits a stereospecific introduction of the key nitrogen functionality at C-4 via an oxazoline intermediate. Three different methods for the final-step conversion of the 4-amino into 4-guanidino derivatives are described. To explore the structure-activity relationship in this region of the molecule, a series of substituted guanidino derivatives were synthesized and their activity is described.