A novel method for the formation of N-glycosides using hydroxamate

✍ Scribed by Jun Nakano; Tsuyoshi Ichiyanagi; Hiromichi Ohta; Yukishige Ito

• Book ID: 104253337
• Publisher: Elsevier Science
• Year: 2003
• Tongue: French
• Weight: 105 KB
• Volume: 44
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(03)00473-8

✦ Synopsis

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 SmI 2 gave Asn-linked glucose. Carbamate derived hydroxamates proved to have even enhanced reactivity to give N-glycosides in high yields.