Preparation and Reactions of Glycosyl Fluorides

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.