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Trimethylsilylnitrate−Trimethylsilyl Azide: A Novel Reagent System for the Synthesis of 2-Deoxyglycosyl Azides from Glycals. Application in the Synthesis of 2-Deoxy-β- N -glycopeptides

✍ Scribed by Reddy, B. Gopal; Madhusudanan, K. P.; Vankar, Yashwant D.

Book ID: 120397212
Publisher: American Chemical Society
Year: 2004
Tongue: English
Weight: 94 KB
Volume: 69
Category: Article
ISSN: 0022-3263
DOI: 10.1021/jo0354948

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Glycals can be readily hydrated using the LaCl 3 •7H 2 O/NaI/PhCH 2 OH reagent system. In one case, having an exo methylene group, such hydration gives an intermediate which is readily converted into 1,6-dideoxynojirimycin, a potential enzyme inhibitor.