Selective isopropylidenation of the 2,3- and 5,6-hydroxy groups of 1-[(tert-butoxycarbonyl)amino]-1-deoxy-D-glucitol 5b led to the diacetonide 6 which was converted in seven steps to the selectively protected 6-azido compound 3, a valuable precursor of various derivatives of 6-amino-1,6-dideoxynojirimycin 4b.
A. Kilonda, F. Compernolle, S. Toppet and G. J. Hoornaert, J. Chem. Soc., Chem. Commun., 1994, 2147 DOI: 10.1039/C39940002147
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