Access to 3-O-Functionalized N-Acetylneuraminic Acid Scaffolds
Author(s)
Pascolutti, Mauro
Madge, Paul D
Thomson, Robin J
von Itzstein, Mark
Year published
2015
Metadata
Show full item recordAbstract
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.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.
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Journal Title
Journal of Organic Chemistry
Volume
80
Issue
15
Subject
Medicinal and biomolecular chemistry
Organic chemistry
Organic chemistry not elsewhere classified
Acid scaffolds
Sialic acids
Glycosides