Preparation of S-glycoside surfactants and cysteine thioglycosides using minimally competent Lewis acid catalysis

Lajos Z. Szabó, Dillon J. Hanrahan, Evan M. Jones, Erin Martin, Jeanne E. Pemberton, Robin Polt

Research output: Contribution to journalArticlepeer-review

8 Scopus citations

Abstract

Here we report a method for the preparation of anomerically pure β-S-glycopyranosides (1,2-trans-glycosides) from the corresponding peracetate donors. S-glycosylation was performed in CHCl 3 at reflux in the presence of a catalytic amount of InBr 3 . Deacylation of the intermediate peracetates were achieved under Zemplén conditions. Five pyranose examples, monosaccharides D-glucose and D-galactose and disaccharides cellobiose, maltose, and lactose, were used as donors, and five thiols including an α/ω dithiol and Fmoc-L-cysteine were used as acceptors. Melting points, high res MS, [α] D and NMR data ( 1 H and 13 C, including COSY, HSQC and HMBC) are reported for compounds not previously described.

Original languageEnglish (US)
Pages (from-to)1-4
Number of pages4
JournalCarbohydrate Research
Volume422
DOIs
StatePublished - Mar 3 2016

Keywords

  • Glycolipid
  • Glycosylated cysteine
  • InBr
  • S-glycosidic linkage
  • Surfactant
  • Thioglycoside

ASJC Scopus subject areas

  • Analytical Chemistry
  • Biochemistry
  • Organic Chemistry

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