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Synlett 1995; 1995(11): 1187-1188
DOI: 10.1055/s-1995-5202
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Asymmetric Synthesis of 6-Deoxy-D-allonojirimycin, D-fuconojirimycin and Their 1-Deoxy Derivatives

Albert Defoin* , Hervé Sarazin, Jacques Streith
  • *Ecole National Supérieure de Chimie de Mulhouse, Université de Haute-Alsace, 3, rue Alfred Werner, F-68093 Mulhouse Cedex, France, Fax (0033) 89 59 98 59; E-mail: J.Streith@uni-mulhouse.fr
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Publication Date:
31 December 2000 (online)

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Asymmetric Diels-Alder reaction of the chiral chloro-nitroso derivative 3 of the D-mannose, with hexadienal dimethylacetal 4b gave the chiral adduct 5a with excellent d.e. This cycloadduct was N-protected and osmylated to give enantiomerically pure diol 6. Simple chemical transformations gave the 6-deoxy-D-allonojirimycin and its 1-deoxy derivative. Double inversion of the bistriflate of 6 led to the D-fuconojirimycin and its 1-deoxy derivative.

6-deoxy-D-allonojirimycin - D-fuconojirimycin - asymmetric Diels-Alder - chiral chloro-nitroso compound - bis-triflate inversion