Chiral water-soluble cyclophanes

C.S. Wilcox and his research team designed and synthesized chiral water-soluble cyclophanes based on carbohydrate precursors. These compounds are also dubbed as glycophanes and they are potentially valuable enzyme models. The key macrocyclization step utilized the Glaser coupling and the reaction was carried out in a thermal flow reactor at 80 °C in 67% yield. 

Bukownik, R. R., Wilcox, C. S. Synthetic receptors. 3,6-anhydro-7-benzenesulfonamido-1,7-dideoxy-4,5-0-isopropylidene-D-altro-hept-1-ynitol a useful component for the preparation of chiral water-soluble cyclophanes based on carbohydrate precursors. J. Org. Chem. 1988, 53, 463 67. 

Figure 78 A chiral, water-soluble cyclophane for enantioselective binding [104]...

Murakami et al. have reported binding studies on (4Z, 15Z)-bilirubin IXa and pamoic acid with a water-soluble, chiral, cage-type cyclophane (Figure 78)... 

Georgiadis, T. M., Georgiadis, M. M., and Diedeiich, F. (1991) Synthesis and Complexation Properties of a Water-Soluble Optically Active Cyclophane Incorporating a 4-Naphthyl-1,2,3,4-tetrahydroisoquinoline Unit as a Chiral Spacer , J. Org. Chem. 56, 3362-3369. 

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