期刊
CHEMISTRY-A EUROPEAN JOURNAL
卷 15, 期 28, 页码 6894-6901出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.200900064
关键词
carbohydrates; cations; cleavage reactions; Friedel-Crafts reaction; reduction
资金
- Japan Society for Promotion of Science [19590032, 21590036]
- RIKEN
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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