title: Direct synthesis of diastereomerically pure glycosyl sulfonium salts.
abstract: It is reported that stable glycosyl sulfonium salts can be generated via direct anomeric S-methylation of ethylthioglycosides. Mechanistically, this pathway represents the first step in the activation of thioglycosides for glycosidation; however, it can further allow for the synthesis and isolation of quasi-stable sulfonium ions, representing a new approach for studying these key intermediates.
authors.affiliation: Department of Chemistry and Biochemistry, University of Missouri-St. Louis, St. Louis, Missouri 63121, United States.
authors.forename: Laurel K
authors.initials: LK
authors.lastname: Mydock
authors.forename: Medha N
authors.initials: MN
authors.lastname: Kamat
authors.forename: Alexei V
authors.initials: AV
authors.lastname: Demchenko
mesh_terms: D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D013237:Stereoisomerism; D013452:Sulfonium Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013865:Thioglycosides / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D013452:Sulfonium Compounds; D013865:Thioglycosides