Copper (II)??Mediated Activation of Sugar Oxazolines: Mild and Efficient Synthesis of β??Glycosides of N??Acetylglucosamine

V Wittmann, D Lennartz

Index: Wittmann, Valentin; Lennartz, Dirk European Journal of Organic Chemistry, 2002 , # 8 p. 1363 - 1367

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Citation Number: 19

Abstract

Abstract 2-Methyl-(3, 4, 6-tri-O-acetyl-1, 2-dideoxy-α-D-glucopyrano)[2, 1-d]-2-oxazoline (5) was reacted with glycosyl acceptors bearing primary (6, 8, 10, 20) or secondary hydroxy groups (12, 14, 16, 18) in the presence of anhydrous cupric bromide or cupric chloride at elevated temperature to provide 2-acetamido-2-deoxy-β-D-glucopyranosides in 36− 92% yield. The reaction conditions are milder than those previously described for oxazoline ...