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Highly Stereoselective Synthesis of the 1-O-Acylglycosyl Ester of Diclofenac via Glycosyl Phosphorothioates, -Selenoates and -Dithioates as Glycosyl Donors

✍ Scribed by Borowiecka, Joanna

Publisher: John Wiley and Sons
Year: 1997
Tongue: English
Weight: 418 KB
Volume: 1997
Category: Article
ISSN: 0947-3440
DOI: 10.1002/jlac.199719971017

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✦ Synopsis

Abstract

Stereoselective glycosylation of o‐(2,6‐dichloroanilino)phenylacetic acid (Diclofenac, 1), as a free carboxylic acid with glycosylthio (2a–c), ‐dithio (3a–e) and ‐selenophosphates (4a–c) as glycosyl donors is reported. The reactions were carried out in aprotic solvents, in the presence of silver carbonate as a leaving group activator. 1‐O‐Acyl sugars 7a–e, new derivatives of Diclofenac, were obtained in high yields as stable, crystalline compounds.

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