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- Title
The Development of an Aza-C-Glycoside Library Based on a Tandem Staudinger/Aza-Wittig/Ugi Three-Component Reaction.
- Authors
Wennekes, Tom; Bonger, Kimberly M.; Vogel, Katrin; van den Berg, Richard J. B. H. N.; Strijland, Anneke; Donker-Koopman, Wilma E.; Aerts, Johannes M. F. G.; van der Marel, Gijsbert A.; Overkleeft, Herman S.
- Abstract
We report the tandem Staudinger/aza-Wittig/Ugi three-component reaction mediated synthesis of a 64-member compound library of aza-C-glycosides. The library is composed of four pyrrolidine and three piperidine scaffolds, onto which a number of functional groups is grafted to form seven sublibraries. Variation in the library is achieved by transformation of two pentoses and a hexose into the corresponding 4-azidopentanal and 5-azidohexanal derivatives as precursors for the Staudinger/aza-Wittig process. Further variation is achieved by using different isocyanides as well as protective- and functional-group manipulations on the fully protected Ugi-3CR intermediates. Preliminary biological evaluation of the compound library revealed several low micromolar inhibitors of human acid glucosylceramidase.
- Publication
European Journal of Organic Chemistry, 2012, Vol 2012, Issue 32, p6420
- ISSN
1434-193X
- Publication type
Article
- DOI
10.1002/ejoc.201200923