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Here we describe the successful syntheses of a series of 4-, 7-, 8- and 9-deoxygenated 2,3-difluoro-N-acetylneuraminic acid derivatives as potential mechanism-based inhibitors of sialidases. The syntheses commenced utilising an enzyme-catalysed aldolase reaction between N-acetyl mannosamine and β-fluoropyruvic acid to give 3-fluoro-N-acetyl-neuraminic acid. This common intermediate was then used in selective protection protocols and Barton–McCombie deoxygenations to generate the complete set of mono-deoxygenated 3-fluoro-N-acetylneuraminic acid derivatives. Finally, a fluorination step utilising (diethylamino)sulfur trifluoride (DAST) was used to successfully generate each of the target difluorides.
|Number of pages||6|
|Early online date||2 Apr 2013|
|Publication status||Published - 7 Jun 2013|
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- 1 Finished
NOVEL ANTI INFLUENZA AGENTS TO TARGET DRUG-INDUCED RESISTANC E: MECHANISM-BASED NEURAMINIDASE INHIBITORS
1/12/06 → 30/11/09
Project: Research council