One-pot regioselective synthesis of 2~Ⅰ,3~Ⅰ-O-(o-xylylene)-capped cyclomaltooligosaccharides: tailoring the topology and supramolecular properties of cyclodextrins

摘要

The a,a'-dibromo-o-xylylene cap has been installed at the secondary hydroxyls of a single glucopyranosyl residue in cyclodextrins in one pot and with total regioselectivity; the resulting cyclic ether acts as a removable hinge, allowing selective elaboration of the secondary face and modulating both the self-association and the inclusion capabilities of the hosts.rnApplications of cyclomaltooligosaccharide (cyclodextrin, CD) derivatives in fields such as site-specific drug delivery, artificial enzymes, catalysis, molecular machines or supramolecular sensing critically depend on the development of efficient methods to manipulate their topology and recognition features with the environment.