Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 53, Issue 31, Pages 8190-8194Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201403543
Keywords
conformation analysis; homogeneous catalysis; glycosides; protecting groups; synthetic methods
Categories
Funding
- GSK
- EPSRC [EP/G036764/1, EP/L001926/1, EP/J002542/1]
- SFI
- Marie-Curie COFUND for a SIRG [11/SIRG//B2154]
- EPSRC [EP/L001926/1, EP/J002542/1, EP/K03927X/1] Funding Source: UKRI
- Science Foundation Ireland (SFI) [11/SIRG/B2154] Funding Source: Science Foundation Ireland (SFI)
- Engineering and Physical Sciences Research Council [EP/J002542/1, EP/K03927X/1, EP/L001926/1] Funding Source: researchfish
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A practical approach has been developed to convert glucals and rhamnals into disaccharides or glycoconjugates with high alpha-selectivity and yields (77-97%) using a trans-fused cyclic 3,4-O-disiloxane protecting group and TsOH center dot H2O (1 mol%) as a catalyst. Control of the anomeric selectivity arises from conformational locking of the intermediate oxacarbenium cation. Glucals outperform rhamnals because the C6 side-chain conformation augments the selectivity.
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