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.

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► 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.