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Strukturelle Abwandlungen anN-Acetylneuraminsäure, 4. Mitt. Transformationen am Diethyl-dithioketal desN-Acetylneuraminsäure-γ-lactons

Transformations on the diethyldithioketal ofN-acetylneuraminic acid-γ-lactone

  • Organische Chemie Und Biochemie
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Abstract

Partial protection of diethyldithioketal ofN-acetylneuraminic acid-γ-lactone using one or two equivalents oft-butyldimethylchlorosilane leads to the 9-O-silyletherderivative7 and the 8,9-bis-O-silylderivative5, resp. The reaction of1 as well as7 with 1,3-dichloro-1,1,3,3-tetraisopropyldisiloxane (TIPSiCl2) yields selectively the protected products4 and9. The 9,8,7,6-tetra-O-acetyl-N-acetylneuraminic acid-γ-lactone derivative3 is formed by the oxidative desulfurazation of the peracteylated form of1 (i. e.2) by means ofNBS. By reaction of5 withTPPDEAD the 6,7-carbonato compound6 arises instead of the expected 6,7-epoxyderivative. The analogous carbonate8 is formed by treating7 with bisimidazolylcarbonate.

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Authors and Affiliations

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

    Erich Zbiral & Walther Schmid

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  1. Erich Zbiral
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  2. Walther Schmid
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Zbiral, E., Schmid, W. Strukturelle Abwandlungen anN-Acetylneuraminsäure, 4. Mitt. Transformationen am Diethyl-dithioketal desN-Acetylneuraminsäure-γ-lactons. Monatsh Chem 116, 253–262 (1985). https://doi.org/10.1007/BF00798461

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  • DOI: https://doi.org/10.1007/BF00798461

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