Synthesis of S‑Linked Glycoconjugates and S‑Disaccharides by Thiol–Ene Coupling Reaction of Enoses

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 fu...

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Veröffentlicht in:Organic letters 2012-09, Vol.14 (17), p.4650-4653
Hauptverfasser: Lázár, László, Csávás, Magdolna, Herczeg, Mihály, Herczegh, Pál, Borbás, Anikó
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Sprache:eng
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Zusammenfassung: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol302098u