Synthesis and Reactions of Anhydro-Azido-thio-D-lyxofuranosides¹

2,5-anhydro-3-azido-2-thio-D-lyxofuranosides and 3,5-anhydro-2-azido-3-thio-D-lyxofuranosides were prepared from methyl D-xylofuranoside or methyl D-ribofuranoside via corresponding 2,3-epoxysugars or the 5-O-trityl derivative. The sulfur was introduced into molecules by use of the thio-Mitsunobu reaction. Bicyclic azido-thiosugars were transformed into nucleoside analogues, oxidized to sulfoxides and sulfones, and reduced to bicyclic amino-thiosugars. Structures and configurations of products were determined by NMR spectroscopy or X-ray structure analyses.

Keywords:

• Azides
• cyclization
• oxidation
• Thiosugars
• X-ray diffraction

Acknowledgments

The University of Hamburg and the Fonds der Chemischen Industrie are gratefully acknowledged for their financial support.