Asymmetric Synthesis of 6-Deoxy-D-allonojirimycin, D-fuconojirimycin and Their 1-Deoxy Derivatives

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Abstract
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.

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