The Journal of organic chemistry

Traceless Staudinger ligation of glycosyl azides with triaryl phosphines: Stereoselective synthesis of glycosyl amides

A Bianchi, A Bernardi

Index: Bianchi, Aldo; Bernardi, Anna Journal of Organic Chemistry, 2006 ,  vol. 71,  # 12  p. 4565 - 4577

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Citation Number: 90

Abstract

α-Glycosyl amides can be synthesized from the corresponding O-benzyl-α-glycosyl azides using a traceless Staudinger ligation with diphenylphosphanyl-phenyl esters 4. All the phosphines employed and their phenol precursors are stable to air at 4° C for months. Fast intramolecular trapping of the reduction intermediates results in the direct formation of the amide link, which, in turn, prevents epimerisation and allows retention of configuration at ...