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

Mauro Pascolutti, Paul D Madge, Robin J Thomson, Mark von Itzstein

J Org Chem. 2015 Aug 7;80(15):7746-51.

PMID: 26118975

Abstract:

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.

Chemicals Related in the Paper:

Catalog Number Product Name Structure CAS Number Price
ALP131486 N-Acetylneuraminic acid N-Acetylneuraminic acid 131-48-6 (anhydrous) Price
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