Stereoselective synthesis of α- and β-glycosylamide derivatives from glycopyranosyl azides via isoxazoline intermediates

被引:143
作者
Damkaci, F [1 ]
DeShong, P [1 ]
机构
[1] Univ Maryland, Dept Chem & Biochem, College Pk, MD 20742 USA
关键词
D O I
10.1021/ja028694u
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Treatment of 2-acetoxy glycopyranosyl azides with Ph3P gave isoxazolines by ring closure of the phosphorimine. Coupling of in situ generated isoxazolines with acylating reagents gave mixtures of α- or β-glycopyranosyl amides. The α/β ratio depended upon the acylating reagent and metal salts employed. For example, coupling of isoxazoline 3 with Z-Asp-(SPy)-OBn in the presence of CuCl2 gave exclusively α-N-glucopyranosylasparagine derivative 8. This general procedure has been applied to mono-, di-, and trisaccharide systems. Copyright © 2003 American Chemical Society.
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页码:4408 / 4409
页数:2
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