Synthesis of thiomaltooligosaccharides by a thio-click approach

László Lázár, A. Borbás, L. Somsák

Research output: Contribution to journalArticle

3 Citations (Scopus)

Abstract

Phenyl 2,3,6,2′,3′,6′-hexa-O-acetyl-4′-S-acetyl-1,4,4′-trithio-β-D-maltoside and its tri-, tetra- and pentasaccharide homologues were prepared by completely regio- and stereoselective photoinitiated thiol-ene coupling reactions of 2-acetoxy-glucal and 4-thioglucose type reaction partners. Complex protecting group strategies could be avoided since all thiols and glucals were prepared from a single starting material, phenyl 2,3,6-tri-O-acetyl-4-S-acetyl-1,4-dithio-β-D-glucopyranoside. The method represents a simple alternative to the known syntheses of similar products.

Original languageEnglish
Pages (from-to)8-12
Number of pages5
JournalCarbohydrate Research
Volume470
DOIs
Publication statusPublished - Dec 1 2018

Keywords

  • Hydrothiolation
  • Radical reactions
  • S-glycosides
  • Thiol-ene additions
  • α-S-linked oligosaccharides

ASJC Scopus subject areas

  • Analytical Chemistry
  • Biochemistry
  • Organic Chemistry

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