Regio- and stereoselective organocatalyzed relay glycosylations to synthesize 2-amino-2-deoxy-1,3-dithioglycosides

Wan, Y.Y.; Zhou, M.M.; Wang, L.M.; Hu, K.X.; Liu, D.Y.; Liu, H.; ... ; Zhang, Q.J. (2023)

Article / Letter to editor

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.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.

• All authors: Wan, Y.Y.; Zhou, M.M.; Wang, L.M.; Hu, K.X.; Liu, D.Y.; Liu, H.; Sun, J.S.; Codee, J.D.C.; Zhang, Q.J.
• Date: 2023-05-16
• Journal: Organic Letters
• Volume: 25
• Issue: 20
• Pages: 3611 - 3617
• DOI: doi:10.1021/acs.orglett.3c00859
• Link: https://pubs.acs.org/doi/10.1021/acs.orglett.3c00859