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Updated: May 22, 2026

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Fluorine-directed β-galactosylation: chemical glycosylation development by molecular editing
Estelle Durantie1, Christoph Bucher, Ryan Gilmour
1Laboratory for Organic Chemistry, Swiss Federal Institute of Technology (ETH) Zürich, 8093 Zürich, Switzerland.
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).
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