title: β-Arabinofuranosylation using 5-O-(2-quinolinecarbonyl) substituted ethyl thioglycoside donors.
abstract: A new β-stereoselective D- and L-arabinofuranosylation method has been developed employing 5-O-(2-quinolinecarbonyl) substituted arabinosyl ethyl thioglycosides as glycosyl donors. The approach allows a wide range of acceptor substrates to be used; the β-selectivity is good-to-excellent. Stereoselective synthesis of a mannose-capped octasaccharide portion from a mycobacterial cell wall polysaccharide was then carried out to demonstrate the utility of this methodology.
authors.affiliation: Key Laboratory of Drug Targeting and Drug Delivery Systems of the Ministry of Education, Department of Chemistry of Medicinal Natural Products, West China School of Pharmacy, Sichuan University, Chengdu 610041, China.
authors.forename: Qiang-Wei
authors.initials: QW
authors.lastname: Liu
authors.forename: Hua-Chao
authors.initials: HC
authors.lastname: Bin
authors.forename: Jin-Song
authors.initials: JS
authors.lastname: Yang
mesh_terms: D001089:Arabinose / Q000737:chemistry*; D006031:Glycosylation; D011134:Polysaccharides / Q000138:chemical synthesis* / Q000737:chemistry; D011804:Quinolines / Q000737:chemistry*; D013237:Stereoisomerism; D013865:Thioglycosides / Q000138:chemical synthesis* / Q000737:chemistry*
chemical_list: D011134:Polysaccharides; D011804:Quinolines; D013865:Thioglycosides; D001089:Arabinose