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Koenigs–Knorr Glycosylation Reaction Catalyzed by Trimethylsilyl Trifluoromethanesulfonate
Author(s) -
Singh Yashapal,
Demchenko Alexei V.
Publication year - 2019
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.201805527
Subject(s) - trimethylsilyl trifluoromethanesulfonate , glycosyl , chemistry , catalysis , glycosylation , trifluoromethanesulfonate , reactivity (psychology) , trimethylsilyl , organic chemistry , reaction conditions , oxide , medicinal chemistry , combinatorial chemistry , biochemistry , medicine , alternative medicine , pathology
The discovery that traditional silver(I)‐oxide‐promoted glycosidations of glycosyl bromides (Koenigs–Knorr reaction) can be greatly accelerated in the presence of catalytic trimethylsilyl trifluoromethanesulfonate (TMSOTf) is reported. The reaction conditions are very mild that allowed for maintaining a practically neutral pH and, at the same time, providing high rates and excellent glycosylation yields. In addition, unusual reactivity trends among a series of differentially protected glycosyl bromides were documented. In particular, benzoylated α‐bromides were much more reactive than their benzylated counterparts under these conditions.