Efficient method for the preparation of peracetylated Neu5Ac2en by flash vacuum pyrolysis.
Peracetylated Neu5Ac2en methyl ester, an intermediate in the synthesis of the influenza neuraminidase inhibitor Relenza, has been synthesized in high yields from peracetylated Neu5Ac methyl ester by flash vacuum pyrolysis. Mechanistic evidence including deuterium labeled studies and DFT (B3LYP) calculations suggest this transformation proceeds via an intramolecular syn-elimination.
Horn
Evan J
EJ
Department of Chemistry, University of California-Davis, One Shields Avenue, Davis, California 95616, USA. horne@uci.edu
Gervay-Hague
Jacquelyn
J
D000107:Acetylation; D000998:Antiviral Agents; D004791:Enzyme Inhibitors / Q000737:chemistry; D006361:Heating; D008722:Methods; D019158:N-Acetylneuraminic Acid / Q000031:analogs & derivatives* / Q000737:chemistry; D009439:Neuraminidase / Q000037:antagonists & inhibitors; D055601:Organic Chemistry Phenomena; D014618:Vacuum; D053243:Zanamivir
D000998:Antiviral Agents; D004791:Enzyme Inhibitors; C036137:2-deoxy-2,3-dehydro-N-acetylneuraminic acid; D009439:Neuraminidase; D019158:N-Acetylneuraminic Acid; D053243:Zanamivir