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Synthesis of All Eight L ‐Glycopyranosyl Donors Using CH Activation
Author(s) -
Frihed Tobias Gylling,
Pedersen Christian Marcus,
Bols Mikael
Publication year - 2014
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201408209
Subject(s) - chemistry , glycosylation , intramolecular force , iridium , acetylation , catalysis , silylation , stereochemistry , biochemistry , gene
The synthesis of all eight rare, but biologically important L ‐hexoses as the according thioglycosyl donors was achieved through a procedure involving the CH activation of their corresponding 6‐deoxy‐ L ‐hexoses. The key steps of the procedure were the silylation of the OH group at C4 followed by an intramolecular CH activation of the methyl group in γ‐position; both steps were catalyzed by iridium. The following Fleming–Tamao oxidation and acetylation gave the suitably protected L ‐hexoses. This is the first general method for the preparation of all eight L ‐hexoses as their thioglycosyl donors ready for glycosylation and the first example of an iridium‐catalyzed C(sp 3 )H activation on sulfide‐containing compounds.