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

Article abstract of DOI:10.1016/0008-6215(89)80003-5

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.