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Formation of septanoses from hexopyranosides via 5,6-exo-glycals
Olivier Jackowski1, Françoise Chrétien, Claude Didierjean
1UMR 7565 SRSMC, Nancy Université-CNRS, Groupe SUCRES, BP 70239, F-54506 Nancy Vandœuvre, France.
Abstract:
Methyl D-hexo-5-ulosides are obtained in high yield by dihydroxylation of 5,6-exo-glucal compounds. The bicyclic structure (1,6-anhydropyrano-5-ulose) of the products is adopted in solution and in solid state in a (4)C(1) conformation. This methodology has been used to prepare 1,6-anhydro-L-idopyrano-5-uloses. Further manipulation of the 1,6-anhydro bridge allowed the preparation of the yet unknown septano-5-uloses in moderate to high yields.
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