132867-65-3

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 
• 108-24-7 acetic anhydride 
• 132867-64-2 (methyl 5,7-O-benzylidene-3-C-cyano-3-deoxy-D-glycero-α-D-ido-heptoseptano)<2,3-d>-oxazolidin-2-one 

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.