Gas chromatography – mass spectrometry of osulose derivatives: O-trimethylsilyl, O-acetyl, O-isopropylidene, methyl glycosides, and 1,1-dimethyl acetals

Abstract

Structure determination of the O-trimethylsilyl, O-acetyl, and O-isopropylidene derivatives of some hexosuloses, pentosuloses, and one tetrosulose, as well as their methyl glycosides and 1,1-dimethyl acetals has been achieved by gas chromatography – mass spectrometry.By study based on the qualitative and quantitative differences in the 36 derivatives obtained, and their analogues prepared from tetradeuterio methanol and/or hexadeuterio acetone, and comparison with results reported in the literature, criteria for the unambiguous determination of the structural grouping are proposed. The relative abundance of each compound when the osulose forms more than one isomeric derivative in the same reaction, as well as chromatographic data for the isolated products, are reported.