The synthesis of a series of deoxygenated 2,3-difluoro-N-acetylneuraminic acid derivatives as potential sialidase inhibitors

Stefan Hader, Andrew Watts

Research output: Contribution to journalArticlepeer-review

9 Citations (Scopus)

Abstract

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.
Original languageEnglish
Pages (from-to)23-28
Number of pages6
JournalCarbohydrate Research
Volume374
Early online date2 Apr 2013
DOIs
Publication statusPublished - 7 Jun 2013

Fingerprint Dive into the research topics of 'The synthesis of a series of deoxygenated 2,3-difluoro-<em>N-</em>acetylneuraminic acid derivatives as potential sialidase inhibitors'. Together they form a unique fingerprint.

Cite this