1437796-22-9

Upstream product

• 1437796-21-8 methyl 5-N-acetyl-2,4,7-tri-O-acetyl-9-O-benzoyl-3,5-dideoxy-3-fluoro-8-O-(phenoxy)thiocarbonyl-D-erythro-α-L-manno-non-2-ulopyranosonate 
• 1437796-20-7 methyl 5-N-acetyl-2,4,7-tri-O-acetyl-9-O-benzoyl-3,5-dideoxy-3-fluoro-D-erythro-α-L-manno-non-2-ulopyranosonate 
• 1437796-19-4 methyl 5-N-acetyl-2,4,7-tri-O-acetyl-3,5-dideoxy-3-fluoro-8,9-O-isopropylidene-D-erythro-α-L-manno-non-2-ulopyranosonate 
• 14131-64-7 N-acetyl-D-mannosamine 
• 1214912-85-2 methyl 5-N-acetyl-3,5-dideoxy-3-fluoro-8,9-O-isopropylidene-D-erythro-α-L-manno-non-2-ulopyranosonate 

Downstream Products

• 1437796-23-0 methyl 5-N-acetyl-4,7-di-O-acetyl-9-O-benzoyl-3,5,8-trideoxy-3-fluoro-D-erythro-α-L-manno-non-2-ulopyranosonate 

Relevant academic research and scientific papers

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

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.