We are interested in developing novel synthetic methodologies to modify cyclodextrins. We have reported the unprecedented per-tritylation of CDs. Due to the superior stability of trityl group towards bases, the per-6-O-tritylation should prove to be a very valuable methody that complements the only few methodologies available for per-6-functionalizations.
We have discovered that (DIBAL-H) reagent can be used to selectively remove 1-2 silyl groups from per-6-O-silylated CD derivatives with high regio- and chemoselectivities.[2-3]
In addition, we have also found that the diisobutylaluminum hydride (DIBAL-H) can be used to remove 3-4 benzyl groups from per-O-benzylated CD derivatives in distinct regioselectivities.[4-5]
- R. Ghosh, P. Zhang, A. Wang, C.-C. Ling. Diisobutylaluminum Hydride-Mediated Regioselective O-Desilylations as a Novel Route to Access Multisubstituted Cyclodextrins. Angew. Chem. Int. Ed., 51, 1548-1552 (2012).
- G. K. Rawal, S. Rani and C.-C. Ling. Unexpected Tri- and Tetra-debenzylation of Perbenzylated a-Cyclodextrin. Tetrahedron Lett., 50, 4633-4636 (2009).
- R. Ghosh, C. Hennigan and C.-C. Ling. DIBAL-H-mediated O-desilylation with highly sterically hindered cyclodextrin substrates. Tetrahedron, 69, 5227-5233 (2013).
- G. K. Rawal, S. Rani, S. Ward and C.-C. Ling. DIBAL-H mediated triple and quadruple debenzylations reactions of perbenzylated cyclodextrins. Org. Biomol. Chem., 8, 171-180 (2010).
Information courtesy of The Ling Research Group Web Page http://www.ucalgary.ca/ccling/research/current-projects/cyclodextrin-chemistry/multiple-substitutions
For more information on this specific project, please contact Dr. Elizabeth Nanak at firstname.lastname@example.org