Journal
TETRAHEDRON LETTERS
Volume 50, Issue 16, Pages 1803-1805Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2009.01.155
Keywords
Aminoglycosides; Glycomimetics; Fluorine; Epoxidation
Categories
Funding
- Perigene Inc.
- Association pour la Recherche contre le Cancer
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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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