Conformational analysis in carbohydrate chemistry. V. Formation of glycosidic anhydrides from heptoses
Open Access
- 15 January 1981
- journal article
- Published by Canadian Science Publishing in Canadian Journal of Chemistry
- Vol. 59 (2) , 379-383
- https://doi.org/10.1139/v81-058
Abstract
The position of the equilibrium between aldoheptoses and their glycosidic anhydrides depends crucially on the configuration of the heptose. Depending on that configuration, the 1,6-anhydropyranose, the 1,7-anhydropyranose, or the 1,6-anhydrofuranose is the major product, its proportion varying from 99% to less than 1%. The position of the equilibrium is predictable from conformational considerations. 1,7-Anhydrofuranoses have not been encountered. The 1,3-dioxane ring of the 1,7-anhydropyranoses was found to assume a skew form.Keywords
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