title: Synthesis of S-linked glycoconjugates and S-disaccharides by thiol-ene coupling reaction of enoses.
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.
authors.affiliation: Research Group for Carbohydrates, University of Debrecen, P.O. Box 94, H-4010 Debrecen, Hungary.
authors.forename: László
authors.initials: L
authors.lastname: Lázár
authors.forename: Magdolna
authors.initials: M
authors.lastname: Csávás
authors.forename: Mihály
authors.initials: M
authors.lastname: Herczeg
authors.forename: Pál
authors.initials: P
authors.lastname: Herczegh
authors.forename: Anikó
authors.initials: A
authors.lastname: Borbás
mesh_terms: D000596:Amino Acids / Q000737:chemistry; D020650:Combinatorial Chemistry Techniques; D004187:Disaccharides / Q000138:chemical synthesis* / Q000737:chemistry; D005942:Gluconates / Q000737:chemistry; D006001:Glycoconjugates / Q000138:chemical synthesis* / Q000737:chemistry; D006031:Glycosylation; D006601:Hexoses / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism; D013438:Sulfhydryl Compounds / Q000737:chemistry*; D013863:Thioglucosides / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000596:Amino Acids; D004187:Disaccharides; D005942:Gluconates; D006001:Glycoconjugates; D006601:Hexoses; D013438:Sulfhydryl Compounds; D013863:Thioglucosides