title: Fluorine-directed β-galactosylation: chemical glycosylation development by molecular editing.
abstract: Validation of the 2-fluoro substituent as an inert steering group to control chemical glycosylation is presented. A molecular editing study has revealed that the exceptional levels of diastereocontrol in glycosylation processes by using 2-fluoro-3,4,6-tri-O-benzyl glucopyranosyl trichloroacetimidate (TCA) scaffolds are a consequence of the 2R,3S,4S stereotriad. This study has also revealed that epimerization at C4, results in a substantial enhancement in β-selectivity (up to β/α 300:1).
authors.affiliation: Laboratory for Organic Chemistry, Swiss Federal Institute of Technology (ETH) Zürich, 8093 Zürich, Switzerland.
authors.forename: Estelle
authors.initials: E
authors.lastname: Durantie
authors.forename: Christoph
authors.initials: C
authors.lastname: Bucher
authors.forename: Ryan
authors.initials: R
authors.lastname: Gilmour
mesh_terms: D020650:Combinatorial Chemistry Techniques; D005461:Fluorine / Q000737:chemistry*; D005697:Galactosides / Q000138:chemical synthesis* / Q000737:chemistry; D006031:Glycosylation; D006845:Hydrocarbons, Fluorinated / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D005697:Galactosides; D006845:Hydrocarbons, Fluorinated; D005461:Fluorine