Synthetic assembly of two β-cyclodextrins through a trehalose moiety as a linker

Abstract

Synthetic assembly of two β-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 SN2 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.