Conformationally superarmed S-ethyl glycosyl donors as effective building blocks for chemoselective oligosaccharide synthesis in one pot

Authors

Mithila Bandara, University of Missouri–St. Louis
Jagodige Yasomanee, University of Missouri–St. Louis
Nigam Rath, University of Missouri–St. Louis
Christian Pedersen, University of Copenhagen
Mikael Bols, University of Copenhagen
Alexei Demchenko, University of Missouri–St. Louis

Document Type

Article

Abstract

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.

Publication Date

November 2016

Publication Title

Organic and Biomolecular Chemistry

Volume

15

Issue

3

First Page

559

Last Page

563

Comments

10.1039/c6ob02498j

DOI

10.1039/C6OB02498J

Recommended Citation

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.
DOI: https://doi.org/10.1039/C6OB02498J
Available at: https://irl.umsl.edu/chemistry-faculty/64