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Conformation of Glycosyl Radicals: Radical Stabilization by β‐CO Bonds
Author(s) -
Dupuis Jacques,
Giese Bernd,
Rüegge Daniel,
Fischer Hanns,
Korth HansGert,
Sustmann Reiner
Publication year - 1984
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.198408961
Subject(s) - radical , chemistry , glycosyl , stereochemistry , stereoselectivity , linkage (software) , organic chemistry , catalysis , biochemistry , gene
A transformation from the chair‐ into the boat conformation takes place when glucosides such as 1 are converted into glucosyl radicals 2 . This preference for the boat conformation is due to the radical‐stabilizing effect of the coplanar arrangement of the β‐CO bond and semi‐occupied orbital. The findings are of interest regarding stereoselective radical CC‐linkage in the synthesis of C‐glycosides.