SYNTHESIS OF 2-ACETAMIDO-1,2,4-TRIDEOXY-1,4-IMINO-D-GALACTITOL AND 2-ACETAMIDO-1,2,4-TRIDEOXY-1,4-IMINO-D-GLUCITOL FOR EVALUATION AS GLYCOSIDASE INHIBITORS

The title compounds, galacto-1 and gluco-2, were synthesised from N-acetyl-D-glucosamine via a common 1,4-diol intermediate that underwent transformations involving either a single or double inversion of stereochemistry at C-4, respectively. In the double inversion sequence, the first inversion involved participation by a t-butyloxycarbonylamino group in an intramolecular sulfonate displacement reaction with the formation of a novel cyclic carbamate.