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Issue 21, 2019
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Synthesis of vicinal dideoxy-difluorinated galactoses

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Abstract

Fluorinated carbohydrates have been employed as probes for fundamental studies of protein–carbohydrate interactions, but also in the development of mechanism-based enzyme inhibitors. There is a continuing demand for novel fluorinated carbohydrate probes. Whereas most examples so far involved monodeoxyfluorinated sugars, multiply deoxyfluorinated sugars have gained much interest. Here we report the synthesis and characterisation of novel vicinal dideoxy-difluorinated D-galactoses with fluorination at the 3,4-positions, and at the 2,3-positions, the latter in both the pyranose and furanose forms. This includes a successful pyranose-into-furanose isomerisation protocol.

Graphical abstract: Synthesis of vicinal dideoxy-difluorinated galactoses

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Publication details

The article was received on 27 Mar 2019, accepted on 08 May 2019 and first published on 16 May 2019


Article type: Paper
DOI: 10.1039/C9OB00707E
Org. Biomol. Chem., 2019,17, 5331-5340

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    Synthesis of vicinal dideoxy-difluorinated galactoses

    J. Malassis, J. Vendeville, Q. Nguyen, M. Boujon, Q. Gaignard-Gaillard, M. Light and B. Linclau, Org. Biomol. Chem., 2019, 17, 5331
    DOI: 10.1039/C9OB00707E

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