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Synlett 1991; 1991(10): 707-708
DOI: 10.1055/s-1991-34767
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A Concise Conversion of Glucose to a Chiral Erythrose Derivative and a Stereospecific Synthesis of 3-Amino-4-cyclohexyl-2-hydroxybutanoates

Tsutomu Inokuchi* , Shinichi Tanigawa, Masafumi Kanazaki, Sigeru Torii
  • *Department of Applied Chemistry, Faculty of Engineering, Okayama University, Okayama 700, Japan
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Publikationsdatum:
13. März 2002 (online)

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Electrooxidation of a D-glucose derivative followed by Baeyer-Villiger oxidation leads to an erythrose derivative. Thus cyclohexylnorstatines 11 are derived from D-glucose in about 10% overall yield via cyclohexylation at the C(6) position, azidation at the C(5) carbon, and cleavage of the C(2)-C(3) bond by the electrooxidation/Baeyer-Villiger oxidation sequence.