title: Glycosidation of thioglycosides in the presence of bromine: mechanism, reactivity, and stereoselectivity.
abstract: Elaborating on previous studies by Lemieux for highly reactive "armed" bromides, we discovered that β-bromide of the superdisarmed (2-O-benzyl-3,4,6-tri-O-benzoyl) series can be directly obtained from the thioglycoside precursor. When this bromide is glycosidated, α-glycosides form exclusively; however, the yields of such transformations may be low due to the competing anomerization into α-bromide that is totally unreactive under the established reaction conditions.
authors.affiliation: Department of Chemistry and Biochemistry, University of Missouri-St. Louis, One University Boulevard, St. Louis, Missouri 63121, United States.
authors.forename: Sophon
authors.initials: S
authors.lastname: Kaeothip
authors.forename: Jagodige P
authors.initials: JP
authors.lastname: Yasomanee
authors.forename: Alexei V
authors.initials: AV
authors.lastname: Demchenko