Glycosyl phosphites as glycosylation reagents: scope and mechanism

H Kondo, S Aoki, Y Ichikawa, RL Halcomb…

Index: Kondo, Hirosato; Aoki, Shin; Ichikawa, Yoshitaka; Halcomb, Randall L.; Ritzen, Helena; Wong, Chi-Huey Journal of Organic Chemistry, 1994 , vol. 59, # 4 p. 864 - 877

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Citation Number: 127

Abstract

The glycosylation reactions with glycosyl phosphites in the presence of catalytic amounts of TMSOTf at low temperature have been studied with different donors and acceptors for the synthesis of several glycosides, including 0-glycosides, S-glycosides, C-glycosides, and glycopeptides. Mechanistic investigations of the reactions indicate that the glycosyl phosphite is activated by either TfOH or TMSOTf, depending on how the substrates are ...

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