F. Nicotra
1997
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0
Influential Citations
137
Citations
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Journal
Topics in Current Chemistry
Abstract
This review article deals with C-glycosides, their biological interest and the synthetic methods for their preparation. C-Glycosides are carbohydrate analogs in which a carbon atom substitutes the oxygen involved in the glycosidic linkage. This modification compromises the anomeric reactivity of the sugar, giving rise to antimetabolites that can inhibit carbohydrate processing enzymes. The synthesis of C-glycosides can be performed from natural sugars, or from non-carbohydrate chiral starting materials. In the first case, the most common, the electrophilic character of the anomeric carbon is in general exploited, in reactions with proper carbon-nucleophiles. In this review, the different C-glycosylation procedures will be classified, and the stereochemical outcome of the reactions highlighted and explained. Particular attention will be paid to the uneasy syntheses of C-glycosides of aminosugars and of non-reducing disaccharides, and to the syntheses of C-glycosides of specific biological interest, such as the phosphono analogs of glycosyl phosphates.