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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.

Original publication

DOI

10.1016/S0040-4020(99)00138-6

Type

Journal article

Journal

Tetrahedron

Publication Date

01/01/1999

Volume

55

Pages

4501 - 4520