Synthesis of 4-epi-2-deoxy-2-Heq-N-acetylneuraminic acid and 2,4-dideoxy-2-Heq N-acetylneuraminic acid

We have continued our work to develop novel analogues of sialic acid [1–4] that may specifically modulate the interaction between endogenous sialic acid and influenza virus haemagglutinin [3,5,6]. Functional groups of sialic acid that have been implicated for this virus-host recongnition are the glycerol side chain, N-acetyl group and the axially oriented carboxylic acid function In this report we describe the synthesis of two analogues, namely, 4-epi-2-deoxy-2-Heq-N-acetylneuraminic acid (4-epi-2-d-2-Heq-Neu5Ac) and 2,4-dideoxy-2-Heq-N-acetylneuraminic acid (2,4-d2-2-Heq-Neu5Ac).