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Synlett 1995; 1995(11): 1187-1188
DOI: 10.1055/s-1995-5202
DOI: 10.1055/s-1995-5202
letter
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved.
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or duplication of any kind, translating, preparation of microfilms, and electronic
data processing and storage.Asymmetric Synthesis of 6-Deoxy-D-allonojirimycin, D-fuconojirimycin and Their 1-Deoxy Derivatives
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Publikationsverlauf
Publikationsdatum:
31. Dezember 2000 (online)

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