Synthetic Assembly of Two Β-Cyclodextrins Through a Trehalose Moiety As a Linker

Synthetic assembly of two beta-cyclodextrins (CDs) was efficiently accomplished using a 6,6'-di-iodotrehalose derivative as a unique linker by means of a one-pot reaction in liquid ammonia for Birch reduction and subsequent S(N)2 replacement. The unique sulfide-linked CD dimer displayed a wider hydrophobic region due to the cavity of the CDs and a part of similar structure of a trehalose linker. An inclusion property of the CD dimer was tentatively examined using TNS (2-p-toluidinylnaphthalene-6-sulfonate) as a model guest compound. (C) 2021 Elsevier Ltd. All rights reserved.