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Preparation and Reactions of Glycosyl Fluorides

Jared L. Randall, K. C. Nicolaou

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Abstract

In recent years, fluorinated carbohydrates have been studied intensively, both as biochemical probes and as glycosylating agents. In this paper, the preparation and reactions of glycosyl fluorides will be reviewed with emphasis on the use of glycosyl fluorides prepared from thioglycosides. Applications of this technology to the synthesis of carbohydrate - containing natural products will be presented. Additionally, the novel 1,2-migration reaction induced by diethylaminosulfur trifluoride (DAST) will be discussed.

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What this paper is about

In recent years, fluorinated carbohydrates have been studied intensively, both as biochemical probes and as glycosylating agents. In this paper, the preparation and reactions of glycosyl fluorides will be reviewed with emphasis on the use of glycosyl fluorides prepared from thioglycosides. Applications of this technology to the synthesis of carbohydrate - containing natural products will be presented. Additionally, the novel 1,2-migration reaction induced by diethylaminosulfur trifluoride (DAST) will be discussed.

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OpenAlex reports 18 citations for this work. Citation counts describe recorded attention and do not establish research quality.

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Available abstract

In recent years, fluorinated carbohydrates have been studied intensively, both as biochemical probes and as glycosylating agents. In this paper, the preparation and reactions of glycosyl fluorides will be reviewed with emphasis on the use of glycosyl fluorides prepared from thioglycosides. Applications of this technology to the synthesis of carbohydrate - containing natural products will be presented. Additionally, the novel 1,2-migration reaction induced by diethylaminosulfur trifluoride (DAST) will be discussed.

Key concepts: Glycosyl, Chemistry, Combinatorial chemistry, Organic chemistry

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