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Highly Stereoselective Synthesis of the 1‐ O ‐Acylglycosyl Ester of Diclofenac via Glycosyl Phosphorothioates, ‐Selenoates and ‐Dithioates as Glycosyl Donors
Author(s) -
Borowiecka Joanna
Publication year - 1997
Publication title -
liebigs annalen
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0947-3440
DOI - 10.1002/jlac.199719971017
Subject(s) - chemistry , glycosyl , stereoselectivity , glycosylation , diclofenac , phenylacetic acid , stereochemistry , organic chemistry , catalysis , biochemistry
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.