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

Author(s):
Wan, Y.Y.; Zhou, M.M.; Wang, L.M.; Hu, K.X.; Liu, D.Y.; Liu, H.; Sun, J.S.; Codee, J.D.C. (0000-0003-3531-2138); Zhang, Q.J.
Published
2023
Publication type
Article / Letter to editor

Abstract

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.

Date issued
2023-05-16
Language
English
Publisher
AMER CHEMICAL SOC
Is part of
Organic Letters (2023), Vol. 25, no. 20, p. 3611-3617
hdl
1887/3656833
doi
10.1021/acs.orglett.3c00859
URL
https://pubs.acs.org/doi/10.1021/acs.orglett.3c00859