Regioselective di- and tetra-functionalisation of γ-cyclodextrin using capping methodology

Abstract

Alkylation of γ-cyclodextrin with 3 equiv. of 1,3-bis[bis(4-tert-butylphenyl)chloromethyl]benzene, followed by permethylation afforded selectively a singly capped (A,B), as well as two doubly capped (A,B:D,E and A,B:E,F) methylated γ-CDs. Deprotection with HBF₄ gave quantitatively the corresponding diols and tetrols, which constitute valuable starting compounds for further functionalisation.