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Synthesis of vicinal dideoxy-difluorinated galactoses. 2019
Julien Malassis, and
Jean-Baptiste Vendeville, and
Qui-Hien Nguyen, and
Marie Boujon, and
Quentin Gaignard-Gaillard, and
Mark Light, and
Bruno Linclau
School of Chemistry, University of Southampton, Highfield, Southampton SO171BJ, UK. bruno.linclau@soton.ac.uk.
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.
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