Protecting‐Group‐Free One‐Pot Synthesis of Glycoconjugates Directly from Reducing Sugars |
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| Authors: | David Lim Prof Margaret A Brimble Dr Renata Kowalczyk Dr Andrew J A Watson Prof Antony John Fairbanks |
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| Institution: | 1. Department of Chemistry, University of Canterbury, Private Bag 4800, Christchurch 8140 (New Zealand);2. School of Chemical Sciences and School of Biological Sciences, The University of Auckland, 23 Symonds Street, Auckland 1142 (New Zealand) |
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| Abstract: | The conversion of sugars into glycomimetics typically involves multiple protecting‐group manipulations. The development of methodology allowing the direct aqueous conversion of free sugars into glycosides, and mimics of oligosaccharides and glycoconjugates in a high‐yielding and stereoselective process is highly desirable. The combined use of 2‐azido‐1,3‐dimethylimidazolinium hexafluorophosphate and the Cu‐catalyzed Huisgen cycloaddition allowed the synthesis of a range of glycoconjugates in a one‐step reaction directly from reducing sugars under aqueous conditions. The reaction, which is completely stereoselective, may be applied to the convergent synthesis of triazole‐linked glycosides, oligosaccharides, and glycopeptides. The procedure provides a method for the one‐pot aqueous ligation of oligosaccharides and peptides bearing alkyne side chains. |
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| Keywords: | carbohydrates click chemistry glycopeptides oligosaccharide mimetics triazoles |
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