Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 15, Issue 28, Pages 6894-6901Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.200900064
Keywords
carbohydrates; cations; cleavage reactions; Friedel-Crafts reaction; reduction
Categories
Funding
- Japan Society for Promotion of Science [19590032, 21590036]
- RIKEN
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2,3-trans-carbamate- and -carbonate-carrying pyranosides were very easily anomerised from the beta to the alpha direction in the presence of a Lewis acid compared to other pyranosides. This reaction is caused by endocyclic cleavage of the pyranosides. Evidence for endocyclic cleavage of conformationally restricted pyranosides in the chair form was obtained by intra- and intermolecular Friedel-Crafts reactions, chloride addition, and reduction of the generated cation. On the other hand, pyranosides with the distorted conformation were never cleaved in an endocyclic manner.
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