Carbohydrate Research p. 85 - 96 (1994)
Update date:2022-09-26
Topics:
Zsoldos-Mady, Virag
Pinter, Istvan
Neszmelyi, Andras
Messmer, Andras
Perczel, Andras
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.
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(2010)Doi:10.1021/jacs.1c04389
(2021)Doi:10.1021/jo00173a025
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(2008)Doi:10.1055/s-2005-918963
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