Synthesis of S-linked glycoconjugates and S-disaccharides by thiol-ene coupling reaction of enoses

László Lázár, Magdolna Csávás, Mihály Herczeg, Pál Herczegh, Anikó Borbás

Research output: Contribution to journalArticle

47 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)4650-4653
Number of pages4
JournalOrganic Letters
Volume14
Issue number17
DOIs
Publication statusPublished - Sep 7 2012

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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