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Synthesis of 2-Acetamido-2-deoxy-D-gluconhydroximolactone- and Chitobionhydroximolactone-Derived N-Phenylcarbamates, Potential Inhibitors of β-N-Acetylglucosaminidase

✍ Scribed by Dieter Beer; Jean-Luc Maloisel; Dora M. Rast; Andrea Vasella

Publisher
John Wiley and Sons
Year
1990
Tongue
German
Weight
320 KB
Volume
73
Category
Article
ISSN
0018-019X

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✦ Synopsis

The N-phenylcarbamate 7, derived from 2-acetamido-2-deoxy-~-gluconhydroximo-l,5-lactone (3) and the analogous N-phenylcarbamate 14, derived from chitobionhydroximo-1,5-lactone (10) have been prepared as potential inhibitors of P-N-acetylglucosaminidases. The unambiguous synthesis of the hydroximo-1,5-lactone 3 involves oxidation of the oxime 1, followed by deprotection with Na/NH,.

We thank Sandoz Ltd., Basel, and the Swiss National Science Foundation for generous support.

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