Synthesis of a ‘head-to-tail’ type cyclodextrin dimer linked by a disulfide bridge

Abstract

A 'head-to-tail' type cyclodextrin dimer, where C-3 of one cyclodextrin and C-6 of the other are linked by a disulfide bond, is synthesized using 2,2'-dipyridyl disulfide, which is widely applicable to the preparation of other dimers.

Synthesis and Molecular Recognition of Novel Oligo(ethylenediamino) Bridged Bis(-cyclodextrin)s and Their Copper(II) Complexes: Enhanced Molecular Binding Ability and Selectivity by Multiple Recognition

“…Hence, diverse functional groups such as alkanedioates, [10,11] disulfides, [12,13] dipyridines, [14,15] and imidazole, [16,17] have been used as the linker between two cyclodextrin units. Hence, diverse functional groups such as alkanedioates, [10,11] disulfides, [12,13] dipyridines, [14,15] and imidazole, [16,17] have been used as the linker between two cyclodextrin units.…”

Chemistry and Biology of Terpene Trilactones fromGinkgo Biloba

“…[56][57][58][59][60][61] Independently, Okabe and co-workers determined the structures of GA (1), GB (2), and GC (3) from leaves of G. Biloba by means of X-ray crystallography. [62,63] Another ginkgolide, ginkgolide J (GJ; 4), was isolated from the leaves of G. biloba in 1987. [64] Interestingly, it appears that GJ (4) is only found in the leaves, whereas GM (5) is found only in the root bark.…”

“…[69,70] The absolute configuration of ginkgolides was determined based on the octant rule analysis of 7-oxo-GC 10-monomethyl ether and another ketone derivative by Maruyama et al [59] Okabe and co-workers treated GA (1) with p-bromobenzoyl bromide to give prismatic crystals of 3-mono-p-bromobenzoate, which were submitted to crystallographic studies. [63] Initially, there was a discrepancy in the reported structures of GB (2) and GC (3) with respect to the relative stereochemistry of the hydroxy group at C1, as Maruyama et al concluded that the hydroxy group was in the a configuration, [59] whereas Okabe and co-workers suggested it to be in the b configuration. [62] Detailed NMR spectroscopic studies [71] and X-ray crystal structures of GB (2) and GC (3) [72,73] confirmed the a configuration of 1-OH.…”

The Modular Approach in Supramolecular Chemistry

“…They demonstrated that the same for-Several groups have prepared cyclodextrin dimers for the complexation of guest molecules. The driving forces include favorable van at the secondary side, or (iii) one at the primary and one at the secondary side [31] . The driving forces include favorable van at the secondary side, or (iii) one at the primary and one at the secondary side [31] .…”