Abstract
[reaction: see text] Partially protected thioglycuronic acids are prepared efficiently by chemo- and regioselective oxidation of the corresponding thioglycosides using the TEMPO/BAIB reagent combination. After esterification, the thioglycuronic acids proved to be useful as both donor and acceptor in sulfonium-mediated condensations toward acidic di- and trisaccharides.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Cyclic N-Oxides
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Glucuronides / chemical synthesis
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Glucuronides / chemistry*
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Glycosylation
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Oxidation-Reduction
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Sulfonium Compounds
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Sulfur Compounds / chemical synthesis
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Sulfur Compounds / chemistry*
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Thioglycosides / chemistry
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Trisaccharides / chemical synthesis*
Substances
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Cyclic N-Oxides
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Glucuronides
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Sulfonium Compounds
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Sulfur Compounds
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Thioglycosides
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Trisaccharides
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TEMPO