title: Solvent effects in the nucleophilic substitutions of tetrahydropyran acetals promoted by trimethylsilyl trifluoromethanesulfonate: trichloroethylene as solvent for stereoselective C- and O-glycosylations.
abstract: The selectivities of nucleophilic substitution reactions of tetrahydropyran acetals promoted by trimethylsilyl trifluoromethanesulfonate depend upon the reaction solvent. Polar solvents favor the formation of S(N)1 products, while nonpolar solvents favor S(N)2 products. Trichloroethylene was identified as the solvent most likely to give S(N)2 products in both C- and O-glycosylation reactions.
authors.affiliation: Department of Chemistry, New York University , New York, New York 10003, United States.
authors.forename: Joanna C
authors.initials: JC
authors.lastname: Kendale
authors.forename: Elizabeth M
authors.initials: EM
authors.lastname: Valentín
authors.forename: K A
authors.initials: KA
authors.lastname: Woerpel
mesh_terms: D000080:Acetals / Q000737:chemistry*; D006031:Glycosylation; D008698:Mesylates / Q000737:chemistry*; D015394:Molecular Structure; D012997:Solvents / Q000737:chemistry*; D013237:Stereoisomerism; D014241:Trichloroethylene / Q000737:chemistry*; D014297:Trimethylsilyl Compounds / Q000737:chemistry*
chemical_list: D000080:Acetals; D008698:Mesylates; D012997:Solvents; D014297:Trimethylsilyl Compounds; C053353:trimethylsilyl trifluoromethanesulfonate; D014241:Trichloroethylene