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

Carbohydr Res. 2016 Mar 3:422:1-4. doi: 10.1016/j.carres.2015.12.008. Epub 2016 Jan 6.

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 CHCl3 at reflux in the presence of a catalytic amount of InBr3. 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.

Keywords: Glycolipid; Glycosylated cysteine; InBr(3); S-glycosidic linkage; Surfactant; Thioglycoside.

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Acylation
  • Catalysis
  • Cysteine / chemistry*
  • Indium / chemistry
  • Lewis Acids / chemistry*
  • Surface-Active Agents / chemistry*
  • Thioglycosides / chemistry*

Substances

  • Lewis Acids
  • Surface-Active Agents
  • Thioglycosides
  • indium bromide
  • Indium
  • Cysteine