289884-68-0Relevant articles and documents
Traceless Staudinger Ligation to Introduce Chemical Diversity on β-Lactamase Inhibitors of Second Generation
Arthur, Michel,Atze, Heiner,Bouchet, Flavie,Ethève-Quelquejeu, Mélanie,Iannazzo, Laura
supporting information, p. 7755 - 7758 (2021/10/25)
We explored the traceless Staudinger ligation for the functionalization of the C2 position of second generation β-lactamase inhibitors based on a diazabicyclooctane (DBO) scaffold. Our strategy is based on the synthesis of phosphine phenol esters and thei
Traceless Staudinger ligation of glycosyl azides with triaryl phosphines: Stereoselective synthesis of glycosyl amides
Bianchi, Aldo,Bernardi, Anna
, p. 4565 - 4577 (2007/10/03)
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 the anomeric carbon. Yields and α-selectivity are high when the reaction is performed in polar aprotic solvents. Removal of the benzyl ether protecting groups is achieved by catalytic hydrogenation. α-Glycosyl amides represent a class of virtually unexplored nonhydrolyzable monosaccharide derivatives that may find a useful application as sugar mimics. Conformational studies by NMR spectroscopy confirm that deprotected α-glycosyl amides in the gluco, galacto, and fuco series retain the normal pyranose conformation of the monosaccharide. The reaction of phosphines 4 with tetra-O-acetyl-glycosyl azides is nonstereoconservative, and β-glycosyl amides are obtained in good yields and with complete stereoselectivity starting from both α and β azides.
A "traceless" Staudinger ligation for the chemoselective synthesis of amide bonds
Saxon, Eliana,Armstrong, Joshua I.,Bertozzi, Carolyn R.
, p. 2141 - 2143 (2007/10/03)
equation presented Here we report a novel modification of our previously reported "Staudinger ligation" that generates an amide bond from an azide and a specifically functionalized phosphine. This method for the selective formation of an amide bond, which
