Premium
Un nouveau type de sucres azotés, les gem ‐azo‐alcools. Communication préliminaire
Author(s) -
Tronchet Jean M. J.,
Rachidzadeh Faranak,
Tronchet Jeannine
Publication year - 1974
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19740570107
Subject(s) - chemistry , acylation , stereoselectivity , epimer , catalysis , medicinal chemistry , organic chemistry
Treatment of keto‐sugar p ‐nitrophenylhydrazones with lead tetraacetate led to the corresponding gem ‐azo‐acetates. The reaction is highly stereoselective, only one of the two possible epimers at the new asymmetric carbon being formed in measurable quantity. Catalytic de‐acylation of these gem ‐azo‐acetates yielded, quantitatively, representatives of a new class of nitrogen‐containing sugars: the gem ‐azo‐alcohols. When treated with potassium t ‐butylate, the gem ‐azoacetates underwent a rearrangement with ring expansion leading to N‐aminolactams.