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Structural variations of N-acetylneuraminic acid, 24: Synthesis of the α-methylketoside of 8-oxo-N-acetylneuraminic acid and related derivatives

Strukturelle Variationen an N-Acetylneuraminsäure, 24. Mitt.: Synthese des α-Methylketosids von 8-Oxo-N-acetylneuraminsäure und verwandten Derivaten

  • Organische Chemie Und Biochemie
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Abstract

The synthesis of the sodium 5-acetamido-2,3,5-trideoxy-2,3 didehydro-D-galacto-2,8-nondiulopyranosidonate 8,8-dimethyl acetal (8) and of the methyl-5-acetamido-3,5-dideoxy-α-D-galacto-2,8-nondiulopyranosidonate 8,8 dimethyl acetal (11) as well as of the methyl-5-acetamido-3,5-dideoxy-α-D-galacto-2,8-nondiulopyranosidonic acid (12) is reported involving the easily accessible 8-oxoderivative5. Compounds11 and12, respectively, showed to have glycosidic bond with remarkable stability to acidic conditions.

Zusammenfassung

Es wird ein Zugang zu Natrium-(5-acetamido-2,3,5-trideoxy-2,3-didehydro-D-galacto-2,8-nondiulopyranosid)onat-8,8-dimethylacetal (8), Methyl-5-acetamido-3,5-dideoxy-α-D-galacto-2,8-nondiulopyranosidonat-8,8-dimethyl acetal (11) und Methyl-5-acetamido-3,5-dideoxy-α-D-galacto-2,8-nondiulopyranosidonsäure (12) über ein gemeinsames, leicht herzustellendes 8-Oxo-Sialinsäurederivat5 beschrieben. Die glycosidische Bindung der Verbindungen11 bzw.12 zeigt eine bemerkenswerte Stabilität gegenüber sauren Reaktionbedingungen, welche im Gegensatz zu Beobachtungen an anderen Neuraminsäuremethylketosiden steht.

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Authors and Affiliations

  1. Institut für Organische Chemie, Universität Wien, A-1090, Wien, Austria

    Michael Hartmann & Erich Zbiral

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  1. Michael Hartmann
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  2. Erich Zbiral
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Hartmann, M., Zbiral, E. Structural variations of N-acetylneuraminic acid, 24: Synthesis of the α-methylketoside of 8-oxo-N-acetylneuraminic acid and related derivatives. Monatsh Chem 122, 995–1003 (1991). https://doi.org/10.1007/BF00823430

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  • DOI: https://doi.org/10.1007/BF00823430

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