Stereoselective Synthesis of α- and β-Glycosylamide Derivatives from Glycopyranosyl Azides via Isoxazoline Intermediates
作者： Fehmi Damkaci , Philip DeShong
DOI: 10.1021/JA028694U
关键词:
摘要: Treatment of 2-acetoxy glycopyranosyl azides with Ph3P gave isoxazolines by ring closure the phosphorimine. Coupling in situ generated acylating reagents mixtures α- or β-glycopyranosyl amides. The α/β ratio depended upon reagent and metal salts employed. For example, coupling isoxazoline 3 Z-Asp-(SPy)-OBn presence CuCl2 exclusively α-N-glucopyranosylasparagine derivative 8. This general procedure has been applied to mono-, di-, trisaccharide systems.
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