Synthetic assembly of two β-cyclodextrins through a trehalose moiety as a linker1This work is dedicated to the memory of Professor Hiroyoshi Kuzuhara. (17th August 2021)

• Record Type: Journal Article
• Authors: Ishimaru, Yoshihiro; Saito, Yosuke; Shiraishi, Yoko S.; Esumi, Yasuaki; Terunuma, Daiyo; Kuzuhara, Hiroyoshi; Matsuoka, Koji
• Is Part Of: Tetrahedron letters. Volume 78(2021)
• Publication Date: 2021-08-17
• Subjects: Cyclodextrins -- Trehalose -- Dimers -- Birch reduction -- Sulfides -- Inclusion properties; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2021.153287
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: One-pot reaction by means of Birch reduction followed by Williamson ether synthesis, for thiobenzylated CD and iodo-trehalose proceeded efficiently. CD dimer linked through a trehalose moiety was synthesized. Inclusion properties of the CD-dimer were carried out. The CD-dimer is able to includes one TNS molecule. 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 SN 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.