Synthesis of Core M3 Matriglycan Constituents via an Additive-Controlled 1,2- cis-Xylopyranosylation with O-Xylosyl Imidates as Donors

Tianlu Li; Miaomiao Zhang; Panpan Lv; Yue Yang; Richard R Schmidt; Peng Peng

doi:10.1021/acs.joc.3c02339

Synthesis of Core M3 Matriglycan Constituents via an Additive-Controlled 1,2- cis-Xylopyranosylation with O-Xylosyl Imidates as Donors

J Org Chem. 2024 Jan 5;89(1):804-809. doi: 10.1021/acs.joc.3c02339. Epub 2023 Dec 26.

Authors

Tianlu Li¹, Miaomiao Zhang¹, Panpan Lv¹, Yue Yang¹, Richard R Schmidt², Peng Peng¹

Affiliations

¹ National Glycoengineering Research Center, Shandong Technology Innovation Center of Carbohydrate, Qingdao, Shandong 266237, China.
² Department of Chemistry, University of Konstanz, D-78457 Konstanz, Germany.

PMID: 38146924
DOI: 10.1021/acs.joc.3c02339

Abstract

A highly stereoselective strategy for 1,2-cis-xylopyranoside bond formation was established via a preactivation-based, additive-modulated trichloroacetimidate glycosidation strategy. The current protocol is mild, practical, and successful with various xylopyranosyl donors and glycosyl acceptors, including acceptors that are reported to be less reactive due to steric hindrance. The utility of this method was demonstrated with the facile assembly of matriglycan constituent tetra- and hexasaccharides.