A Solution to Chemical Pseudaminylation via a Bimodal Glycosyl Donor for Highly Stereocontrolled α- and β-Glycosylation

Ruohan Wei; Han Liu; Arthur H Tang; Richard J Payne; Xuechen Li

doi:10.1021/acs.orglett.9b00990

A Solution to Chemical Pseudaminylation via a Bimodal Glycosyl Donor for Highly Stereocontrolled α- and β-Glycosylation

Org Lett. 2019 May 17;21(10):3584-3588. doi: 10.1021/acs.orglett.9b00990. Epub 2019 May 2.

Authors

Ruohan Wei¹, Han Liu¹, Arthur H Tang², Richard J Payne², Xuechen Li¹

Affiliations

¹ Department of Chemistry, State Key Laboratory of Synthetic Chemistry , The University of Hong Kong , Hong Kong , P. R. China.
² School of Chemistry , The University of Sydney , Sydney , Australia.

PMID: 31045367
DOI: 10.1021/acs.orglett.9b00990

Abstract

A robust methodology for the stereocontrolled chemical glycosylation of pseudaminic acid has been developed to afford both α- (axial) and β- (equatorial) glycosides reliably with complete stereoselectivity, using a common glycosyl donor (7 N-Cbz/5 N-azido Pse thioglycoside) simply by changing the reaction conditions. In the CH₂Cl₂/MeCN cosolvent, highly β-selective pseudaminylation was observed, while addition of 5.0 equiv DMF in CH₂Cl₂ gave the α-pseudaminosides.

Publication types

Research Support, Non-U.S. Gov't