N-Aryl-O-glycosyl haloacetimidates as glycosyl donors

U Huchel, P Tiwari, RR Schmidt

Index: Huchel, Uschi; Tiwari, Pallavi; Schmidt, Richard R. Journal of Carbohydrate Chemistry, 2010 , vol. 29, # 2 p. 61 - 75

Full Text: HTML

Citation Number: 13

Abstract

Reaction of 1-O-unprotected tetra-O-acetyl-and tetra-O-benzyl-glucopyranose with N-aryl haloacetimidoyl chlorides in the presence of sodium hydride and 15-crown-5 afforded N-aryl- O-glucopyranosyl haloacetimidates. Mainly the β-anomers were obtained in this anomeric O- acylation-type reaction. The glycosyl donor properties of these haloacetimidates were investigated with 6-O-and 4-O-unprotected glucopyranosides as acceptors. The results ...