✦ LIBER ✦

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-acetamido-methyl-3-tert-butoxycarbonylamino-3-deoxy sugars

✍ Scribed by Francisco Santoyo Gonzalez; Antonio Vargas Berenguel; Fernando Hernandez Mateo; Pilar Garcia Mendoza

Publisher: Elsevier Science
Year: 1991
Tongue: English
Weight: 773 KB
Volume: 209
Category: Article
ISSN: 0008-6215
DOI: 10.1016/0008-6215(91)80151-c

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✦ Synopsis

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-carbamoyL3-cyano-3-deoxy sugars l-4 were transformed into N-protected 3-amino-3-cyano-3-deoxy sugars S-8 by Hofmann rearrangement (lead tetra-acetate-N,Ndimethylformamide-rert-butyl alcohol). Reduction of the cyano group in these compounds (NaBH,-CoC&) gave, after acetylation, the corresponding 1,2-diamino derivatives 13-16.

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