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Evidence for Endocyclic Cleavage of Conformationally Restricted Glycopyranosides
Author(s) -
Manabe Shino,
Ishii Kazuyuki,
Hashizume Daisuke,
Koshino Hiroyuki,
Ito Yukishige
Publication year - 2009
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200900064
Subject(s) - chemistry , cleavage (geology) , stereochemistry , residue (chemistry) , lewis acids and bases , organic chemistry , catalysis , geotechnical engineering , fracture (geology) , engineering
2,3‐ trans ‐carbamate‐ and ‐carbonate‐carrying pyranosides were very easily anomerised from the β to the α 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.