A new series of superarmed glycosyl donors has been investigated. It was demonstrated that the S-ethyl leaving group allows for high reactivity, which is much higher than that of equally equipped S-phenyl glycosyl donors that were previously investigated by our groups. The superarmed S-ethyl glycosyl donors equipped with a 2-O-benzoyl group gave complete β-stereoselectivity. Utility of the new glycosyl donors has been demonstrated in a one-pot one-addition oligosaccharide synthesis with all of the reaction components present from the beginning.
Organic and Biomolecular Chemistry
Bandara, Mithila; Yasomanee, Jagodige; Rath, Nigam; Pedersen, Christian; Bols, Mikael; and Demchenko, Alexei, "Conformationally superarmed S-ethyl glycosyl donors as effective building blocks for chemoselective oligosaccharide synthesis in one pot" (2016). Chemistry & Biochemistry Faculty Works. 64.
Available at: https://irl.umsl.edu/chemistry-faculty/64