title: Aryl(trifluoroethyl)iodonium Triflimide and Nitrile Solvent Systems: A Combination for the Stereoselective Synthesis of Armed 1,2-trans-β-Glycosides at Noncryogenic Temperatures.
abstract: Armed thioglycosides can be activated with aryl(trifluoroethyl)iodonium triflimide in 2:1 CH2Cl2/pivalonitrile or a solvent combination of CH2Cl2, acetonitrile, isobutyronitrile, and pivalonitrile (6:1:1:1) at 0 °C for glycosylation reactions that proceed in good yield and moderate to excellent selectivity (up to 25:1 β/α). Comparison to other common glycosylation promoters reveals that both the mixed solvent and the iodonium salt promoter are required for stereoselectivity.
authors.affiliation: Department of Chemistry, Tufts University , 62 Talbot Avenue, Medford, Massachusetts 02155, United States.
authors.forename: An-Hsiang Adam
authors.initials: AH
authors.lastname: Chu
authors.affiliation: Department of Chemistry, Tufts University , 62 Talbot Avenue, Medford, Massachusetts 02155, United States.
authors.forename: Andrei
authors.initials: A
authors.lastname: Minciunescu
authors.affiliation: Department of Chemistry, Tufts University , 62 Talbot Avenue, Medford, Massachusetts 02155, United States.
authors.forename: Clay S
authors.initials: CS
authors.lastname: Bennett
mesh_terms: D000097:Acetonitriles / Q000737:chemistry; D003512:Cyclohexanones / Q000737:chemistry*; D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry; D006031:Glycosylation; D015394:Molecular Structure; D009570:Nitriles / Q000737:chemistry; D012997:Solvents; D013237:Stereoisomerism; D013696:Temperature; D013865:Thioglycosides / Q000737:chemistry
chemical_list: D000097:Acetonitriles; D003512:Cyclohexanones; D006027:Glycosides; D009570:Nitriles; D012997:Solvents; D013865:Thioglycosides; C518058:triflimide; C022246:isobutyronitrile; C032159:acetonitrile