Formation of septanoses from hexopyranosides via 5,6-exo-glycals

Carbohydrate Research
Olivier JackowskiYves Chapleur

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.

References

Dec 7, 2007·Nucleosides, Nucleotides & Nucleic Acids·David Sabatino, Masad J Damha
May 1, 2008·The Journal of Organic Chemistry·Alma Dzudza, Tobin J Marks

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Citations

Jan 11, 2020·Organic & Biomolecular Chemistry·David GoyardSébastien Vidal

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