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Synthesis of C-glycosides of biological interest

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Glycoscience Synthesis of Substrate Analogs and Mimetics

Part of the book series: Topics in Current Chemistry ((4143,volume 187))

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.

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Authors and Affiliations

  1. Dipartimento di Chimica Organica e Industriale, Università degli Studi di Milano, Via Venezian, 21 I-20133, Milano, Italy

    Francesco Nicotra

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  1. Francesco Nicotra
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Hugues Driguez Joachim Thiem

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© 1997 Springer Verlag Berlin Heidelberg

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Nicotra, F. (1997). Synthesis of C-glycosides of biological interest. In: Driguez, H., Thiem, J. (eds) Glycoscience Synthesis of Substrate Analogs and Mimetics. Topics in Current Chemistry, vol 187. Springer, Berlin, Heidelberg. https://doi.org/10.1007/BFb0119253

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  • DOI: https://doi.org/10.1007/BFb0119253

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  • Publisher Name: Springer, Berlin, Heidelberg

  • Print ISBN: 978-3-540-62032-7

  • Online ISBN: 978-3-540-49628-1

  • eBook Packages: Springer Book Archive

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