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Synlett 1990; 1990(3): 166
DOI: 10.1055/s-1990-21023
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Synthesis of Mannosamine via Cobaloximes

Andreas Veit* , Bernd Giese
  • *Institut für Organische Chemie der Universität Basel, St. Johanns-Ring 19, CH-4056 Basel, Switzerland
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Publication Date:
08 March 2002 (online)

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Reaction of methyl 3,4,6-tri-O-acetyl-2-bromo-2-deoxy-ß-D-glucopyranoside (5) with sodium cobaloxime leads to isomeric carbohydrate cobaloximes. Photolysis in the presence of nitrous oxide followed by selective hydrogenation gives methyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-ß-D-mannopyranoside (9) in good overall yield.