2-ACETAMIDO-2-DEOXYALDONOLACTONES FROM SUGAR FORMAZANS

A new approach towards simple aldonic acid derivatives starting from t he corresponding aldoses via the 2-acetamido-2-deoxy formazans resulte d 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 lac tones and that of the intermediate lactone phenylhydrazone (7) was pro ved by H-1 and C-13 NMR studies, including deuterium-induced different ial isotope shift (DIS) measurements. With sodium borohydride, lactone s 8 and 11 were converted into 2-acetamido-2-deoxy-D-galactitol (15) a nd its 6-deoxy analogue (17), respectively.