title: Preparation of S-glycoside surfactants and cysteine thioglycosides using minimally competent Lewis acid catalysis.
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.
authors.affiliation: Department of Chemistry and Biochemistry, BIO5, The University of Arizona, 1306 E. University Blvd., Tucson, AZ 85721, USA.
authors.forename: Lajos Z
authors.initials: LZ
authors.lastname: Szabó
authors.affiliation: Department of Chemistry and Biochemistry, BIO5, The University of Arizona, 1306 E. University Blvd., Tucson, AZ 85721, USA.
authors.forename: Dillon J
authors.initials: DJ
authors.lastname: Hanrahan
authors.affiliation: Department of Chemistry and Biochemistry, BIO5, The University of Arizona, 1306 E. University Blvd., Tucson, AZ 85721, USA.
authors.forename: Evan M
authors.initials: EM
authors.lastname: Jones
authors.affiliation: Department of Chemistry and Biochemistry, BIO5, The University of Arizona, 1306 E. University Blvd., Tucson, AZ 85721, USA.
authors.forename: Erin
authors.initials: E
authors.lastname: Martin
authors.affiliation: Department of Chemistry and Biochemistry, BIO5, The University of Arizona, 1306 E. University Blvd., Tucson, AZ 85721, USA.
authors.forename: Jeanne E
authors.initials: JE
authors.lastname: Pemberton
authors.affiliation: Department of Chemistry and Biochemistry, BIO5, The University of Arizona, 1306 E. University Blvd., Tucson, AZ 85721, USA. Electronic address: polt@u.arizona.edu.
authors.forename: Robin
authors.initials: R
authors.lastname: Polt
mesh_terms: D000215:Acylation; D002384:Catalysis; D003545:Cysteine / Q000737:chemistry*; D007204:Indium / Q000737:chemistry; D058116:Lewis Acids / Q000737:chemistry*; D013501:Surface-Active Agents / Q000737:chemistry*; D013865:Thioglycosides / Q000737:chemistry*
chemical_list: D058116:Lewis Acids; D013501:Surface-Active Agents; D013865:Thioglycosides; C530781:indium bromide; D007204:Indium; D003545:Cysteine
keywords: Glycolipid; Glycosylated cysteine; InBr(3); S-glycosidic linkage; Surfactant; Thioglycoside