Skip to main content
SpringerLink
Log in

Structural variations of N-Acetylneuraminic acid, 12: A new useful approach to 4-epi- and 8-epi-N-Acetylneuraminic acid

Strukturelle Abwandlungen an N-Acetylneuraminsäure, 12: Eine neue, nützliche Synthese von 4-epi- und 8-epi-N-Acetylneuraminsäure

  • Organische Chemie Und Biochemie
  • Published:
Monatshefte für Chemie / Chemical Monthly Aims and scope Submit manuscript

Summary

Readily available Neu5Ac derivatives1 and7 are oxidized by RuO4 to the ketones2 and8 which are reduced diastereoselectively by the borane-ammonia complex to yield the4- and 8-epimers4a and10. Subsequent deprotection leads to the title compounds5 and12. This few step procedure is also applicable on gram scale.

Zusammenfassung

Die leicht zugänglichen Neuraminsäurederivate1 und7 werden mittels RuO4 in die Ketone2 und8 umgewandelt, welche mit dem Ammoniak-Boran-Komplex diastereoselektiv zu den entsprechenden 4- und 8-Epimeren4 a und10 reduziert werden. Anschließende Deblockierungsschritte führen zu den Titelverbindungen5 und12. Diese Synthesewege sind für den Grammaßstab ausgearbeitet worden.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. Previous commun. (no. 11): Zbiral E., Schreiner E., Salunkhe M. M., Schulz G., Kleineidam R. G., Schauer R. (1989) Liebigs Ann. Chem.: 589

  2. Schauer R. (1982) Cell Biology Monographs, Vol. 10. Springer, Wien New York

    Google Scholar 

  3. Schauer R. (1982) Adv. Carbohydr. Chem. Biochem.40: 132

    Google Scholar 

  4. Brandstetter H. H., Zbiral E. (1983) Liebigs Ann. Chem.: 2055; Gross H. J., Kovac A., Rose U., Watzlawik H., Brossmer R. (1988) Biochemistry27: 4279

  5. Zbiral E., Brandstetter H. H. (1985) Monatsh. Chem.116: 87

    Google Scholar 

  6. Petrik C. R., Korythnyk W. (1981) Anal. Biochem.131: 153; Brossmer R., Rose U., Kasper D., Smith T. L., Grasmuk H., Unger F. M. (1980) Biochem. Biophys. Res. Commun.96: 1282; Gross H. J., Bunsch A., Paulsen J. C., Brossmer R. (1987) Eur. J. Biochem.168: 595

    Google Scholar 

  7. Baumberger F., Vasella A. (1986) Helv. Chim. Acta69: 1205

    Google Scholar 

  8. Courtney J. L. (1986) Ruthenium Tetroxide Oxidations. In: Mijs W. J., de Jonge C. R. H. I. (ed.) Organic Synthesis by Oxidation with Metal Compounds. Plenum Press, New York, p. 464

    Google Scholar 

  9. Salunkhe M. M., Hartmann M., Schmid W., Zbiral E. (1988) Liebigs Ann. Chem.: 187

  10. Babirad S. A., Wong Y., Kishi Y. (1987) J. Org. Chem.52: 1370

    Google Scholar 

  11. Brandstetter H. H., Zbiral E., Schulz G. (1982) Liebigs Ann. Chem.: 1

  12. Reuter G., Schauer R. (1988) Glycoconjugate J.5: 123; Zbiral E., Schreiner E., Salunkhe M. M., Schulz G., Kleineidam R. G., Schauer R. (1989) Liebigs Ann. Chem.: 159

    Google Scholar 

  13. Zilliken F., O'Brien P. J. (1960) Biochem. Prep.7: 1; Martensson E., Raal A., Svennerholm L. S. (1958) Biochim. Biophys. Acta30: 124

    Google Scholar 

  14. Czarniecki M. F., Thornton E. R. (1977) J. Am. Chem. Soc.99: 8273

    Google Scholar 

  15. Kuhn R., Lutz P., MacDonald D. L. (1966) Chem. Ber.99: 611

    Google Scholar 

  16. Still W. C., Kahn M., Mitra A. (1978) J. Org. Chem.43: 2923

    Google Scholar 

  17. Christian R., Schulz G, Brandstetter H. H., Zbiral E. (1987) Carbohydr. Res.162: 1

    Google Scholar 

Download references

Author information

Authors and Affiliations

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

    Michael Hartmann & Erich Zbiral

Authors
  1. Michael Hartmann
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Erich Zbiral
    View author publications

    You can also search for this author in PubMed Google Scholar

Rights and permissions

Reprints and permissions

About this article

Cite this article

Hartmann, M., Zbiral, E. Structural variations of N-Acetylneuraminic acid, 12: A new useful approach to 4-epi- and 8-epi-N-Acetylneuraminic acid. Monatsh Chem 120, 899–906 (1989). https://doi.org/10.1007/BF00811129

Download citation

  • Received:

  • Accepted:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00811129

Keywords

Search

Navigation