Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 53, Issue 50, Pages 13889-13893Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201408209
Keywords
CH activation; Fleming-Tamao oxidation; glycosyl donors; iridium catalysis; L-hexoses
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Funding
- Lundbeck Foundation
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The synthesis of all eight rare, but biologically important L-hexoses as the according thioglycosyl donors was achieved through a procedure involving the CH activation of their corresponding 6-deoxy-L-hexoses. The key steps of the procedure were the silylation of the OH group at C4 followed by an intramolecular CH activation of the methyl group in -position; both steps were catalyzed by iridium. The following Fleming-Tamao oxidation and acetylation gave the suitably protected L-hexoses. This is the first general method for the preparation of all eight L-hexoses as their thioglycosyl donors ready for glycosylation and the first example of an iridium-catalyzed C(sp(3))H activation on sulfide-containing compounds.
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