Synthesis of Cyclophellitol, Cyclophellitol Aziridine, and Their Tagged Derivatives (pages 6030–6043)
Kah-Yee Li, Jianbing Jiang, Martin D. Witte, Wouter W. Kallemeijn, Hans van den Elst, Chung-Sing Wong, Sharina D. Chander, Sascha Hoogendoorn, Thomas J. M. Beenakker, Jeroen D. C. Codée, Johannes M. F. G. Aerts, Gijs A. van der Marel and Herman S. Overkleeft
Article first published online: 14 AUG 2014 | DOI: 10.1002/ejoc.201402588
The syntheses of cyclophellitol and of cyclophellitol aziridine from a common intermediate are described. Optimization of the construction of this building block, previously described by Madsen, enables the synthesis of both title compounds. Azide groups are introduced into both cyclitol cores to allow click ligation to a variety of tags, thus yielding a series of retaining glucosidase probes.