Herein, we describe a novel methodology for the regio-and stereoselectiveconvergent synthesis of 2-amino-2-deoxy-dithioglycosides via one-potrelay glycosylation of 3-O-acetyl-2-nitroglucal donors... Show moreHerein, we describe a novel methodology for the regio-and stereoselectiveconvergent synthesis of 2-amino-2-deoxy-dithioglycosides via one-potrelay glycosylation of 3-O-acetyl-2-nitroglucal donors.This unique organo-catalysis relay glycosylation features excellentsite- and stereoselectivity, good to excellent yields, mild reactionconditions, and broad substrate scope. 2-Amino-2-deoxy-glucosides/mannosidesbearing 1,3-dithio-linkages were efficiently obtained from 3-O-acetyl-2-nitroglucal donors in both stepwise and one-potglycosylation protocols. The dithiolated O-antigen of E. coli serogroup 64 was successfully synthesizedusing this newly developed method. Show less
Herein, we report a new glycosylation system for the highly efficient and stereoselective formation of glycosidic bonds using glycosyl N-phenyl trifluoroacetimidate (PTFAI) donors and a charged... Show moreHerein, we report a new glycosylation system for the highly efficient and stereoselective formation of glycosidic bonds using glycosyl N-phenyl trifluoroacetimidate (PTFAI) donors and a charged thiourea hydrogen-bond-donor catalyst. The glycosylation protocol features broad substrate scope, controllable stereoselectivity, good to excellent yields and exceptionally mild catalysis conditions. Benefitting from the mild reaction conditions, this new hydrogen bond-mediated glycosylation system in combination with a hydrogen bond-mediated aglycon delivery system provides a reliable method for the synthesis of challenging phenolic glycosides. In addition, a chemoselective glycosylation procedure was developed using different imidate donors (trichloroacetimidates, N-phenyl trifluoroacetimidates, N-4-nitrophenyl trifluoroacetimidates, benzoxazolyl imidates and 6-nitro-benzothiazolyl imidates) and it was applied for a trisaccharide synthesis through a novel one-pot single catalyst strategy. Show less
