Abstract

AbstractConversion of disaccharide reducing units into the corresponding methoximes followed by their reduction with NaBH4CN to the corresponding deoxy(methoxyamino)alditol glycosides (RCH2‐NHOCH3) introduces a constitutional asymmetry in the sugar molecule. After methylation of the resulting compounds, cleavage of the glycosidic bonds is carried out by BF3‐ catalyzed methanolysis, affording permethylated O‐methylglycosides and permethylated deoxy(methylmethoxyamino)alditols with a free −OH corresponding to the position of the glycosidic bond. Identification of the reducing moiety is achieved by GC‐FTIR and computerized retrieval of library FTIR spectra.

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