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Issue 7, 2020
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6-Deoxy-6-fluoro galactofuranosides: regioselective glycosylation, unexpected reactivity, and anti-leishmanial activity

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Abstract

Selective glycosylation of the C-6 fluorinated galactofuranosyl acceptor 2 was studied with four galactofuranosyl donors. It was highlighted that this electron-withdrawing atom strongly impacted the behavior of the acceptor, thus leading to unprecedented glycosylation pathways. Competition between expected glycosylation of 2, ring expansion of this acceptor and furanosylation, and intermolecular aglycon transfer was observed. Further investigation of the fluorinated synthetic compounds showed that the presence of fluorine atom contributed to increase the inhibition of the growth of Leishmania tarentolae, a non-pathogenic strain of Leishmania.

Graphical abstract: 6-Deoxy-6-fluoro galactofuranosides: regioselective glycosylation, unexpected reactivity, and anti-leishmanial activity

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Article information


Submitted
05 Dec 2019
Accepted
03 Feb 2020
First published
03 Feb 2020

Org. Biomol. Chem., 2020,18, 1462-1475
Article type
Paper

6-Deoxy-6-fluoro galactofuranosides: regioselective glycosylation, unexpected reactivity, and anti-leishmanial activity

J. Vaugenot, A. El Harras, O. Tasseau, R. Marchal, L. Legentil, B. Le Guennic, T. Benvegnu and V. Ferrières, Org. Biomol. Chem., 2020, 18, 1462
DOI: 10.1039/C9OB02596K

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