One-step conversion of unprotected sugars to β-glycosyl azides using 2-chloroimidazolinium salt in aqueous solution

T Tanaka, H Nagai, M Noguchi, A Kobayashi…

Index: Tanaka, Tomonari; Nagai, Hikaru; Noguchi, Masato; Kobayashi, Atsushi; Shoda, Shin-Ichiro Chemical Communications, 2009 , # 23 p. 3378 - 3379

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Citation Number: 38

Abstract

In a series of our studies on the direct activation of unprotected sugars in aqueous media, 7 we found that 2-chloro-1,3-dimethylimidazolinium chloride (DMC) 8 is an excellent agent for selective activation of the anomeric hydroxy groups. The reactions proceed through a reactive intermediate formed as a result of preferential attack of the anomeric hydroxy group towards DMC, based on the fact that the pK a values of hemiacetal anomeric hydroxy groups are much lower ...