Application of the Hofmann rearrangement in the synthesis of 3-amino sugar derivatives: preparation of some 3-tert-butoxycarbonylamino-3-cyano-3-deoxy and 3-acetamidomethyl-3-tert-butoxycarbonylamino-3-deoxy sugars

Article abstract of DOI:10.1016/0008-6215(91)80151-C

The cyclisation of dialdehydes, obtained from sugars, with cyanoacetamide and subsequent Hofmann rearrangement is a convenient and short approach to the synthesis of 3-amino sugar derivatives branched at C-3.Thus, derivatives of 3-carbamoyl-3-cyano-3-deoxy sugars 1-4 were transformed into N-protected 3-amino-3-cyano-3-deoxy sugars 5-8 by Hofmann rearrangement (lead tetra-acetate-N,N-dimethylformamide-tert-butyl alcohol).Reduction of the cyano group in these compounds (NaBH4-CoCl2) gave, after acetylation, the corresponding 1,2-diamino derivatives 13-16.