Acceptor-influenced and donor-tuned base-promoted glycosylation
Stephan Boettcher1, Martin Matwiejuk, Joachim Thiem
1Department of Chemistry, Faculty of Science, University of Hamburg, Martin-Luther-King-Platz 6, 20146 Hamburg, Germany.
Abstract:
Base-promoted glycosylation is a recently established stereoselective and regioselective approach for the assembly of di- and oligosaccharides by using partially protected acceptors and glycosyl halide donors. Initial studies were performed on partially methylated acceptor and donor moieties as a model system in order to analyze the key principles of oxyanion reactivities. In this work, extended studies on base-promoted glycosylation are presented by using benzyl protective groups in view of preparative applications. Emphases are placed on the influence of the acceptor anomeric configuration and donor reactivities.
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