28876-38-2Relevant articles and documents
2-Acetamido-2-deoxyaldonolactones from sugar formazans
Zsoldos-Mady, Virag,Pinter, Istvan,Neszmelyi, Andras,Messmer, Andras,Perczel, Andras
, p. 85 - 96 (2007/10/02)
A new approach towards simple aldonic acid derivatives starting from the corresponding aldoses via the 2-acetamido-2-deoxy formazans resulted in the synthesis of 2-acetamido-2-deoxy-D-galactono-1,4-lactone (8), and its 6-deoxy (11) and 6-azido-6-deoxy (14) analogues on treatment with trifluoroacetic acid.The five-membered ring structure of the lactones and that of the intermediate lactone phenylhydrazone (7) was proved by 1H and 13C NMR studies, including deuterium-induced differential isotope shift (DIS) measurements.With sodium borohydride, lactones 8 and 11 were converted into 2-acetamido-2-deoxy-D-galactitol (15) and its 6-deoxy analogue (17), respectively.