Access to 3‑O‑Functionalized N‑Acetylneuraminic Acid Scaffolds
journal contributionposted on 07.08.2015 by Mauro Pascolutti, Paul D. Madge, Robin J. Thomson, Mark von Itzstein
Any type of content formally published in an academic journal, usually following a peer-review process.
Direct access to 3-O-functionalized 2-α-N-acetylneuraminides and their corresponding 2,3-dehydro-2-deoxy-N-acetylneuraminic acid derivatives is described. Initially, a stereoselective ring-opening of the key intermediate N-acetylneuraminic acid (Neu5Ac) 2,3-β-epoxide with an alcohol provided the 3-hydroxy α-glycoside. O-Alkylation of the C3 hydroxyl group generated novel 3-O-functionalized Neu5Ac derivatives that provided the corresponding unsaturated derivatives upon elimination.