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 These compounds are stable analogs of the corresponding O-saccharides in which the interglycosidic oxygen has been replaced by a carbon atom.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
Current Organic Chemistry
Title: Synthesis of C-Saccharides and Higher Congeners
Volume: 5 Issue: 12
Author(s): Lei Liu, Michael McKee and Maarten H.D. Postema
Affiliation:
Keywords: C-saccharides, interglycosidic oxygen, anionic chemistry, SIGMATROPIC APPROACHES, Glycals, Nucleophiles, Anionic Addition-Cyclization, Levoglucosenone
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 These compounds are stable analogs of the corresponding O-saccharides in which the interglycosidic oxygen has been replaced by a carbon atom.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.
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Cite this article as:
Liu Lei, McKee Michael and Postema H.D. Maarten, Synthesis of C-Saccharides and Higher Congeners, Current Organic Chemistry 2001; 5 (12) . https://dx.doi.org/10.2174/1385272013374699
DOI https://dx.doi.org/10.2174/1385272013374699 |
Print ISSN 1385-2728 |
Publisher Name Bentham Science Publisher |
Online ISSN 1875-5348 |
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