Current Organic Chemistry

Author(s): Lei Liu, Michael McKee and Maarten H.D. Postema

DOI: 10.2174/1385272013374699

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Synthesis of C-Saccharides and Higher Congeners

Page: [1133 - 1167] Pages: 35

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Abstract

This work reviews the synthesis of a class of stable sugar mimics termed, C-saccharides. These compounds are stable analogs of the corresponding O-saccharides in which the interglycosidic oxygen has been replaced by a carbon atom. For the most part, this review focuses on the synthesis of C-disaccharides. The organization is based on the type of chemistry used to assemble the target and has the following sub-sections: sigmatropic approaches, synthesis based on the cationic reactivity of the anomeric carbon atom, metal-mediated processes, cyclization methodology, processes based on anionic chemistry and methods based on free radical chemistry.

Keywords: C-saccharides, interglycosidic oxygen, anionic chemistry, SIGMATROPIC APPROACHES, Glycals, Nucleophiles, Anionic Addition-Cyclization, Levoglucosenone