Synthesis of C-Saccharides and Higher Congeners

Authors: Liu L.; McKee M.; Postema M.H.D.

Source: Current Organic Chemistry, Volume 5, Number 12, December 2001 , pp. 1133-1167(31)

Publisher: Bentham Science Publishers

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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 These compounds are stable analogs of the corresponding O-saccharides in which the interglycosidic oxygen has been replaced by a carbon atom.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

Language: English

Document Type: Review article

DOI: http://dx.doi.org/10.2174/1385272013374699

Publication date: 2001-12-01