566200-19-9Relevant articles and documents
A novel method for the formation of N-glycosides using hydroxamate
Nakano, Jun,Ichiyanagi, Tsuyoshi,Ohta, Hiromichi,Ito, Yukishige
, p. 2853 - 2856 (2003)
Direct formation of Asn-linked carbohydrate by N-glycosylation has been difficult, because of the lack of nucleophilicity of carboxamide nitrogen. We report here the novel N-glycosylation using Asn hydroxamate as a glycosyl acceptor. Reaction with glycosyl fluoride or glycosyl trichloroacetimidate afforded N-glycoside and subsequent reduction with SmI2 gave Asn-linked glucose. Carbamate derived hydroxamates proved to have even enhanced reactivity to give N-glycosides in high yields.