Synthesis of the Salmonella type E(1) core trisaccharide as a probe for the generality of 1-(benzenesulfinyl)piperidine/triflic anhydride combination for glycosidic bond formation from thioglycosides.
A synthesis of a chromogenic glycoside of the Salmonella anatum group E(1) core trisaccharide is presented in which all three glycosidic bonds, a 1,2-cis-equatorial, a 1,2-trans-axial, and a 1,2-trans-equatorial linkage representing three of the four main classes of glycosidic bond, are formed with thioglycoside donors activated under a single set of conditions by the combination of 1-(benzenesulfinyl)piperidine and trifluoromethanesulfonic anhydride. 2,3-O-Carbonyl- and 2,3-O-isopropylidene-alpha-L-rhamnopyranosyl thioglycosides are found to be highly alpha-selective rhamnosyl donors under these conditions.
Crich
David
D
Department of Chemistry, University of Illinois at Chicago, 845 West Taylor Street, Chicago, Illinois 60607-7061, USA. dcrich@uic.edu
Li
Hongmei
H
D002625:Chemistry, Organic / Q000379:methods; D006031:Glycosylation; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D010880:Piperidines / Q000737:chemistry*; D011135:Polysaccharides, Bacterial / Q000737:chemistry*; D012475:Salmonella / Q000737:chemistry*; D013237:Stereoisomerism; D013865:Thioglycosides / Q000737:chemistry*; D014312:Trisaccharides / Q000138:chemical synthesis*
C469850:1-(benzenesulfinyl)piperidine; D010880:Piperidines; D011135:Polysaccharides, Bacterial; D013865:Thioglycosides; D014312:Trisaccharides