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Approaches to the synthesis of CF2-analogues of 2-deoxy-2-aminoglycosides
Article de revue   Avec comité de lecture

Approaches to the synthesis of CF2-analogues of 2-deoxy-2-aminoglycosides

Florent Poulain, Eric Leclerc et Jean-Charles Quirion
Tetrahedron letters, Vol.50(16), pp.1803-1805
22/04/2009
DOI: https://doi.org/10.1016/j.tetlet.2009.01.155

Résumé

Chemistry Chemistry, Organic Physical Sciences Science & Technology
The preparation of a fluorinated C-glycosidic analogue of a 2-deoxy-2-acetamido-D-altrose is described. The synthetic sequence involves the addition of a difluoroenoxysilane to a D-glucal, an epoxidation of the resulting unsaturated CF2-glycoside and a ring-opening reaction with TMSN3. An Overman rearrangement of the unsaturated intermediate is also described. (C) 2009 Elsevier Ltd. All rights reserved.

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