132867-64-2

Upstream product

• 131367-29-8 methyl 2,4-di-O-acetyl-5,7,O-benzylidene-3-carbamoyl-3-C-cyano-3-deoxy-D-glycero-α-D-ido-heptoseptanoside 
• 132867-55-1 methyl 2,4-di-O-acetyl-5,7-O-benzylidene-3-tert-butoxycarbonylamino-3-C-cyano-3-deoxy-D-glycero-α-D-ido-heptoseptanoside 

Downstream Products

• 132867-65-3 Acetic acid (3aR,4R,4aS,6R,8aR,10S,10aS)-3-acetyl-3a-cyano-10-methoxy-2-oxo-6-phenyl-octahydro-1,5,7,9-tetraoxa-3-aza-benzo[f]azulen-4-yl ester 

Relevant academic research and scientific papers

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

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.