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Synfacts 2007(1): 0033-0033  
DOI: 10.1055/s-2006-955683
Synthesis of Materials and Unnatural Products
© Georg Thieme Verlag Stuttgart · New York

β-Glucopyranoside Cage Receptor

Contributor(s): Timothy M. Swager, Eric L. Dane
O. Francesconi, A. Ienco, G. Moneti, C. Nativi, S. Roelens*
UniversitÀ di Firenze and Istituto di Chimica dei Composti Organometallici, Firenze, Italy
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Publication History

Publication Date:
15 December 2006 (online)

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Significance

A cage compound containing six secondary amines and three pyrrolic rings has been synthesized and used to complex β-gluco­pyranosides. The cage compound is remarkable in that it shows exclusive binding of the β-anomer. The synthesis of the receptor is notable due to its simplicity. The first transformation is driven to completion by the precipitation of the insoluble product. Next, imine reduction occurs in near-quantitative yield.