THIOSUGARS. VIII.^* PREPARATION OF NEW 4′-THIO-L-LYXO PYRIMIDINE NUCLEOSIDE ANALOGUES

Abstract

Reaction of 1-O-acetyl-2,3,5-tri-O-benzyl-4-thio-L-lyxofuranose with silylated pyrimidine bases and subsequent deprotection with boron tribromide led to 4′-thio-L-lyxo pyrimidine nucleosides. The 5-bromo-6-methyl derivative was prepared from methyl 2,3,5-tri-O-acetyl-4-thio-L-lyxofuranoside. Deacetylation was performed with sodium methoxide. The anomers were separated by HPLC and their configurations assigned by NMR spectroscopy and X-ray structural analyses. The biological activity of the nucleosides was tested.

^*Part VII: Wirsching, J., Voss, J., Adiwidjaja, G., Giesler, A., Kopf, J. Eur. J. Org. Chem. 2001, in press.

ACKNOWLEDGMENTS

The Deutsche Forschungsgemeinschaft, the Fonds der Chemischen Industrie and the European Commission are gratefully acknowledged for their financial support. We like to thank the Degussa-Hüls AG for support of this work by supplying silver carbonate. We also thank Prof. Dr. Chris Meier and Dipl.-Chem. Andreas Lomp, University of Hamburg, for making their HPLC equipment available to us. We also thank Mrs. Ann Absillis, Mrs. Anita Camps and Miss Lies Vandenheurck for technical assistance.

Notes

^*Part VII: Wirsching, J., Voss, J., Adiwidjaja, G., Giesler, A., Kopf, J. Eur. J. Org. Chem. 2001, in press.