Journal
TETRAHEDRON
Volume 65, Issue 45, Pages 9474-9480Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2009.08.061
Keywords
Cyclomaltooctaose; Cyclodextrin; Sulfonate; Azido; Regioisomer
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Seven isomers of cyclomaltooctaose (gamma-cyclodextrin) whose C6s were unsymmetrically disubstituted with both an azido group and an arenesulfonyloxy group were prepared and each of them was isolated by reversed phase chromatography. The assignment of the modified positions in each regioisomers was unambiguously performed by chemical correlation with the authentic compounds and chemical conversion to the 3,6-anhydro derivatives followed by high-resolution 2D-H-1 NMR (COSY, TOCSY, and HO-HAHA) analyses. The compounds are versatile synthetic and authentic intermediates to prepare sophisticated derivatives with two different functionalities at desired positions on the molecule for supramolecular chemistry. (C) 2009 Elsevier Ltd. All rights reserved.
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