Conformational analysis in carbohydrate chemistry. V. Formation of glycosidic anhydrides from heptoses

Author:

Angyal Stephen John,Tran Trung Quang

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.

Publisher

Canadian Science Publishing

Subject

Organic Chemistry,General Chemistry,Catalysis

Cited by 8 articles. 订阅此论文施引文献 订阅此论文施引文献,注册后可以免费订阅5篇论文的施引文献,订阅后可以查看论文全部施引文献

1. Stephen John Charles Angyal;Advances in Carbohydrate Chemistry and Biochemistry;2013

2. CHEMISTRY OF ANHYDRO SUGARS;Advances in Carbohydrate Chemistry and Biochemistry;2003

3. H;Dictionary of Carbohydrates;1998

4. A new type of anhydro sugar: 1,3 1 -anhydro-3- C -hydroxymethylaldoses;Carbohydrate Research;1992-09

5. The reactions of 3-deoxy-d-manno-oct-2-ulosonic acid (KDO) in dilute acid;Carbohydrate Research;1987-07

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