Use of cyclic sulfamidates derived from D-allosamine in nucleophilic displacements: Scope and limitations

Article abstract of DOI:10.1016/S0040-4020(97)00246-9

A cyclic 2,3-sulfamidate derived from N-acetyl-D-allosamine has been treated with a variety of S-. N-, O-. and C-nucleophiles, leading to nucleophilic displacement at C-3, elimination, or deacetylation reactions depending on the type of nucleophile used. Nucleophilic displacement is achieved with thio-nucleophiles and NaN₃. allowing the preparation of 3-thio- or 3-azido glucosamine derivatives difficult to obtain by use of sulfonates.