Tetrazoles of manno- and rhamno- furanoses
Davis BG., Nash RJ., Watson AA., Smith C., Fleet GWJ.
The synthesis of [3.3.0] bicyclic tetrazoles derived from D-manno and D- rhamnofuranose staffing from D-mannose, and of L-rhamnofuranose starting from L-rhamnose is described. The key step in the formation of all three examples of this novel class of sugar mimics is an intramolecular [1,3]dipolar cycloaddition of azide and nitrile moieties.