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Protecting group free synthesis of urea-linked glycoconjugates: efficient synthesis of β-urea glycosides in aqueous solution†
Yoshiyasu Ichikawa,Takahiro Minami,Shohei Kusaba,Nobuyoshi Saeki,Yuta Tonegawa,Yumiko Tomita,Keiji Nakano,Hiyoshizo Kotsuki,Toshiya Masuda
Organic & Biomolecular Chemistry Pub Date : 05/02/2014 00:00:00 , DOI:10.1039/C3OB42452A
Abstract

A method for the protecting group free synthesis of β-urea-linked glycoconjugates has been developed. The one step process, involving reactions between urea and D-glucose, N-acetyl-D-glucosamine or D-xylose in acidic aqueous solution, furnishes the corresponding β-urea glycosides in modest yields. This simple and efficient procedure is applicable to the synthesis of β-urea tethered amino acid–carbohydrate conjugates.

Graphical abstract: Protecting group free synthesis of urea-linked glycoconjugates: efficient synthesis of β-urea glycosides in aqueous solution
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