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Synthesis of a O-propargyl glycoside suitable for protein modification by Cu(I)-catalyzed cycloaddition

External protocol Created on 03 May 2014

Authors

Henrik H. Jensen, Holger B. Kramer, and Benjamin G. Davis

Summary

Here we describe the efficient and facile synthesis of N-acetyl glucosamine propargyl O-glycoside, a compound which has been prepared previously by conventional methods.1 In previous syntheses the glycoside was obtained as a mixture of anomers1a) and in moderate to acceptable yield1b). The described improved method exploits a high yielding and strongly β-selective lanthanide triflate catalysed2 glycosylation reaction. In addition to reaction efficiency the method is characterised by its simplicity and facile compound isolation and purification. The propargyl O-glycoside was prepared for its subsequent use in Cu(I) catalysed protein modification reactions.3

Further details

The protocol was published on Protocol Exchange in 2007. To see the entire protocol, click on the source link.

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