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Chemistry of 1,2-Anhydro Sugars

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The 1,2-anhydro sugars are a class of valuable and versatile intermediates in carbohydrate chemistry. In the first part of this article, a review is given on preparation methods of 1,2-anhydro sugars that are suitably protected. Protected 1,2-anhydro sugars have been widely used as glycosyl donors for the synthesis of glycosyl compounds such as oligosaccharides and nucleosides. In the second part, a brief history and the chemistry of unprotected 1,2-anhydro sugars is described. In the past few years, our research group has developed protection-free methods for synthesis of glycosyl compounds through unprotected 1,2-anhydro sugars as reactive intermediates based on the concept of 'direct anomeric activation'. In this article, the one-step preparation of glycosyl compounds such as thioglycoside derivatives and glycosyl azides by using formamidinium-type dehydrating agents is presented. Furthermore, the initial results on the first detection of unprotected 1,2-anhydro sugar intermediates by NMR measurements are shown along with their full structure characterizations.
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Keywords: 1,2-ANHYDRO SUGAR; 2-CHLORO-1,3-DIMETHYLIMIDAZOLINIUM CHLORIDE (DMC); DIRECT ANOMERIC ACTIVATION; GLYCOSYL AZIDE; GLYCOSYL BUNTE-SALT

Document Type: Research Article

Affiliations: 1: Department of Biomolecular Engineering Graduate School of Engineering, Tohoku University Aoba, Sendai 980-8579, Japan 2: Department of Biomolecular Engineering Graduate School of Engineering, Tohoku University Aoba, Sendai 980-8579, Japan;, Email: [email protected]

Publication date: 01 December 2018

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  • International Journal for Chemistry and Official Membership Journal of the Swiss Chemical Society (SCS) and its Divisions

    CHIMIA, a scientific journal for chemistry in the broadest sense, is published 10 times a year and covers the interests of a wide and diverse readership. Contributions from all fields of chemistry and related areas are considered for publication in the form of Review Articles and Notes. A characteristic feature of CHIMIA are the thematic issues, each devoted to an area of great current significance.

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