Photoinitiated hydrothiolation of pyranoid exo-glycals: The d-galacto and d-xylo cases

János József, László Juhász, Tünde Zita Illyés, Magdolna Csávás, Anikó Borbás, László Somsák

Research output: Contribution to journalArticle

14 Citations (Scopus)

Abstract

Radical-mediated addition reactions of thiols to O-peracetylated exo-galactal and exo-xylal with 2,2-dimethoxy-2-phenylacetophenone as the photoinitiator resulted in high yielding formation of the corresponding β-d-glycopyranosylmethyl-sulfide derivatives (2,6-anhydro-1-deoxy-1-S-substituted-1-thio-alditols) with exclusive regio- and very high stereoselectivity, including disaccharide mimicks with Gly-CH2-S-Gly scaffolds.

Original languageEnglish
Pages (from-to)63-69
Number of pages7
JournalCarbohydrate Research
Volume413
DOIs
Publication statusPublished - Jun 22 2015

Keywords

  • Disaccharide mimicks
  • Exo-galactal
  • Exo-xylal
  • Thiol-ene click reaction

ASJC Scopus subject areas

  • Analytical Chemistry
  • Biochemistry
  • Organic Chemistry

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