Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 76, Issue 9, Pages 3366-3371Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo2003055
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- Grants-in-Aid for Scientific Research [23655124, 22350072] Funding Source: KAKEN
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A macrocyclic host molecule having pyridine-pyridone-pyridine modules for saccharide recognition was prepared by Cu(II)-mediated oxidative homocoupling of a tandem diethynyl precursor. In CH2Cl2, the host molecule associated with dodecyl beta-maltoside much more strongly K-a = 1.4 x 10(6) M-1) than with octyl monohexosides (K-a = ca. 2 x 10(3) to 1 x 10(4) M-1), accompanied with induced CDs. An all-pyridine macrocyclic host was also studied, and its binding strength with saccharides was weaker than that for the pyridine-pyridone-pyridine host.
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