Abstract
Free-radical hydrothiolation of the endocyclic double bond of enoses is reported. Reaction between 2-acetoxy-D-glucal and a range of thiols including amino acid, peptide, glycosyl thiols, and sugars with primary or secondary thiol functions gave S-linked α-glucoconjugates and S-disaccharides with full regio- and stereoselectivity. Addition of glycosyl thiols to a 2,3-unsaturated glycoside also proceeded with good selectivity and afforded a series of 3-deoxy-S-disaccharides.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Amino Acids / chemistry
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Combinatorial Chemistry Techniques
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Disaccharides / chemical synthesis*
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Disaccharides / chemistry
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Gluconates / chemistry
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Glycoconjugates / chemical synthesis*
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Glycoconjugates / chemistry
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Glycosylation
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Hexoses / chemistry*
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Molecular Structure
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Stereoisomerism
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Sulfhydryl Compounds / chemistry*
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Thioglucosides / chemical synthesis*
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Thioglucosides / chemistry
Substances
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Amino Acids
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Disaccharides
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Gluconates
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Glycoconjugates
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Hexoses
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Sulfhydryl Compounds
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Thioglucosides