Issue 21, 2019

Synthesis of vicinal dideoxy-difluorinated galactoses

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

Supplementary files

Article information

Article type
Paper
Submitted
27 Mar 2019
Accepted
08 May 2019
First published
16 May 2019

Org. Biomol. Chem., 2019,17, 5331-5340

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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