Chiral reagents in glycosylation and modification of carbohydrates

Carbohydrates play a significant role in numerous biological events, and the chemical synthesis of carbohydrates is vital for further studies to understand their various biological functions. Due to the structural complexity of carbohydrates, the stereoselective formation of glycosidic linkages and...

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Bibliographic Details
Published in:Chemical Society reviews 2018-02, Vol.47 (3), p.681-71
Main Authors: Wang, Hao-Yuan, Blaszczyk, Stephanie A, Xiao, Guozhi, Tang, Weiping
Format: Article
Language:English
Subjects:
Carbohydrates
Chemical synthesis
Hydroxyl groups
Oligosaccharides
Polysaccharides
Reagents
Stereoselectivity
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Summary:Carbohydrates play a significant role in numerous biological events, and the chemical synthesis of carbohydrates is vital for further studies to understand their various biological functions. Due to the structural complexity of carbohydrates, the stereoselective formation of glycosidic linkages and the site-selective modification of hydroxyl groups are very challenging and at the same time extremely important. In recent years, the rapid development of chiral reagents including both chiral auxiliaries and chiral catalysts has significantly improved the stereoselectivity for glycosylation reactions and the site-selectivity for the modification of carbohydrates. These new tools will greatly facilitate the efficient synthesis of oligosaccharides, polysaccharides, and glycoconjugates. In this tutorial review, we will summarize these advances and highlight the most recent examples. This review summarizes recent advances in stereoselective glycosylation and site-selective functionalization of carbohydrates mediated by chiral reagents including chiral auxiliaries and chiral catalysts.
ISSN:0306-0012
1460-4744
DOI:10.1039/c7cs00432j