Characterization of cyclomalto-hexaose and -heptaose derivatives by the reductive-cleavage method

Abstract

The substitution patterns of cyclomalto-hexaose and -heptaose derivatives carrying alkyl, acyl, and carbamoyl substituents have been investigated by the reductive-cleavage method. The modified cyclomalto-hexaoses or -heptaoses were treated with triethylsilane and trimethylsilyl trifluoromethanesulfonate to give the corresponding 1,5- and 1,4-anhydroglucitol derivatives that were acetylated or, in the case of acetyl derivatives, trifluoroacetylated and analysed by g.l.c.-m.s. For the alkylated compounds, minute amounts of products formed by under- or over-alkylation, or of isomeric components, could be detected. Partial reduction of the acyloxy groups to alkyloxy groups and cleavage of acyl substituents were observed. Carbamoyl substituents were stable under the conditions of reductive cleavage.