Synthesis and properties of cyclo-α-1,4-manno-2,3-epoxides

Publisher Website
Google Scholar
Abstract
Treatment of per-2-O-tosyl-cyclodextrins with K2CO3 allows the synthesis of cyclomannoepoxides 2a, 2b, 2c in high yields (>90%). The glucopyranose structure of 2a, 2b, 2c, is assigned from the 1H coupling pattern (J1,2 = 0 Hz, J2,3 = 3.5 Hz, J3,4 = 0 Hz), as a half chair conformation. 2b shows surfactant properties in water. Full analysis of the NMR spectra of 2a, 2b, 2c has been carried out. The inclusion and hydrolytic properties of 2 differ from those of the parent cyclodextrins as a result of a lack of secondary hydroxyl groups capable of forming hydrogen-bonded dimers.