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Synlett 1995; 1995(8): 803-805
DOI: 10.1055/s-1995-5098
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The Synthesis of 4-amino-4-deoxy-D-mannose and Glucosamine: A New Methodology for the Design of Homochiral Amino Sugars from non-Carbohydrate Precursors

Kevin Pitzer, Tomas Kudlicky*
  • *Department of Chemistry, Virginia Polytechnic Institute and State University, Blacksburg, VA 24061-0212, USA
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Publikationsdatum:
31. Dezember 2000 (online)

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A new methodology for the synthesis of amino sugars from non-carbohydrate precursors (derived from chlorobenzene) is described. The key step involves the ozonolysis of vinyl halides of type 1 and subsequent reductive regio- and stereo controlled recyclization to form amino pyranose derivatives.

amino sugars - glucosamine - 4-amino-4-deoxymannose - cyclohexadiene-cis-diols