Fluorine‐Directed β‐Galactosylation: Chemical Glycosylation Development by Molecular Editing | Zendy

Durantie Estelle | Zendy; Bucher Christoph | Zendy; Gilmour Ryan | Zendy

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Fluorine‐Directed β‐Galactosylation: Chemical Glycosylation Development by Molecular Editing

Author(s) -

Durantie Estelle,

Bucher Christoph,

Gilmour Ryan

Publication year - 2012

Publication title -

chemistry – a european journal

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.687

H-Index - 242

eISSN - 1521-3765

pISSN - 0947-6539

DOI - 10.1002/chem.201200468

Subject(s) - glycosylation , epimer , substituent , chemistry , selectivity , stereochemistry , combinatorial chemistry , biochemistry , catalysis

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 2 R ,3 S ,4 S 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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