Stereoselective synthesis of N-galactofuranosyl amides

α- or β-Galactofuranosyl (Galf) amides can be synthesized with high stereoselectivity by traceless Staudinger ligation starting from unprotected β-galactofuranosyl azide or tetra-O-acetyl-β-galactofuranosyl azide, respectively. The resulting Galf amides are hitherto unknown molecules, with interesting potential as inhibitors of mycobacterial growth.

Graphical abstractsdFigure optionsDownload full-size imageDownload as PowerPoint slideResearch highlights► Staudinger ligation of β-galactofuranosyl azides affords Galf amides, a hitherto unknown class of molecules. ► 1,2-cis Galactofuranosylamides are obtained from the unprotected azide. ► 1,2-trans Galactofuranosylamides are obtained from the tetra-O-acetyl azide.