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Access to 3‑O‑Functionalized N‑Acetylneuraminic Acid Scaffolds

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journal contribution
posted on 07.08.2015 by Mauro Pascolutti, Paul D. Madge, Robin J. Thomson, Mark von Itzstein
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.