title: Fluorine-directed 1,2-trans glycosylation of rare sugars.
abstract: To reconcile the urgent need to access well defined β-configured 2,6-di-deoxypyranose analogues for chemical biology, with the intrinsic α-selectivity of the native system, the directing role of fluorine at C2 has been explored. Localised partial charge inversion (C-H(δ+)→ C-F(δ-)) elicits a reversal of the substrate-based α-stereoselectivity, irrespective of the protecting group electronics.
authors.affiliation: Institute for Organic Chemistry and Excellence Cluster EXC 1003 "Cells in Motion", Westfälische Wilhelms-Universität Münster, Corrensstraße 40, 48149 Münster, Germany. ryan.gilmour@uni-muenster.de.
authors.forename: Nuria
authors.initials: N
authors.lastname: Aiguabella
authors.forename: Mareike C
authors.initials: MC
authors.lastname: Holland
authors.forename: Ryan
authors.initials: R
authors.lastname: Gilmour
mesh_terms: D002236:Carbohydrate Conformation; D005461:Fluorine / Q000737:chemistry*; D006031:Glycosylation; D008958:Models, Molecular; D013237:Stereoisomerism; D000073893:Sugars / Q000737:chemistry*
chemical_list: D000073893:Sugars; D005461:Fluorine