ω-Aldehydo Sugars Prepared by Ninhydrin Oxidation

Abstract

The reaction of ninhydrin with 6-amino-6-deoxy-hexopyranosyl sugars has been investigated. 6-Aldehydocyclohexaamylose and 1,2:3,4-di-O-isopropylidene-α-D-galacto-hexodialdo-1,5-pyranose have been prepared by oxidative deamination of 6-amino-deoxycyclohexaamylose and 6-amino-6-deoxy-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose, respectively, using ninhydrin. The preparation of the two aldehydes by the ninhydrin reaction is compared with the method of photolysis of the corresponding azido sugars. The mass spectra of the perdimethylsilyl derivatives of cyclohexaamylose and O-methyl oxime of 6-aldehydocyclohexaamylose have been recorded.