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2-Acetamido-2-deoxyaldonolactones from sugar formazans

✍ Scribed by Virág Zsoldos-Mády; István Pintér; András Neszmélyi; András Messmer; András Perczel

Publisher: Elsevier Science
Year: 1994
Tongue: English
Weight: 682 KB
Volume: 252
Category: Article
ISSN: 0008-6215
DOI: 10.1016/0008-6215(94)90007-8

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✦ Synopsis

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-o-galactono-1,4lactone (81, 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 'H and 13C NMR studies, including deuterium-induced differential isotope shift (DIS) measurements.

With sodium borohydride, lactones 8 and 11 were converted into 2acetamido-2-deoxy-o-galactitol (15) and its 6-deoxy analogue (171, respectively.

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