title: De Novo Asymmetric Synthesis of a 6-O-Methyl-D-glycero-L-gluco-heptopyranose-Derived Thioglycoside for the Preparation of Campylobacter jejuni NCTC11168 Capsular Polysaccharide Fragments.
abstract: An enantioselective de novo synthesis of a thioglycoside derivative of the 6-O-methyl-D-glycero-L-gluco-heptopyranose residue found in the Campylobacter jejuni NCTC11168 (HS:2) capsular polysaccharide is reported. The compound is obtained from a furfural-derived chiral diol in 11 steps. Notably, compared to the only previous synthesis of this molecule, this approach significantly reduces the number of purification steps required to obtain the target.
authors.affiliation: Alberta Glycomics Centre and Department of Chemistry, The University of Alberta , Edmonton, Alberta T6G 2G2, Canada.
authors.forename: Roger A
authors.initials: RA
authors.lastname: Ashmus
authors.affiliation: Alberta Glycomics Centre and Department of Chemistry, The University of Alberta , Edmonton, Alberta T6G 2G2, Canada.
authors.forename: Anushka B
authors.initials: AB
authors.lastname: Jayasuriya
authors.affiliation: Alberta Glycomics Centre and Department of Chemistry, The University of Alberta , Edmonton, Alberta T6G 2G2, Canada.
authors.forename: Ying-Jie
authors.initials: YJ
authors.lastname: Lim
authors.affiliation: Department of Chemistry, Northeastern University , 360 Huntington Ave., Boston, Massachusetts 02115, United States.
authors.forename: George A
authors.initials: GA
authors.lastname: O'Doherty
authors.affiliation: Alberta Glycomics Centre and Department of Chemistry, The University of Alberta , Edmonton, Alberta T6G 2G2, Canada.
authors.forename: Todd L
authors.initials: TL
authors.lastname: Lowary
mesh_terms: D016667:Bacterial Capsules / Q000737:chemistry; D016123:Campylobacter jejuni / Q000737:chemistry*; D005990:Glycerol / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D009005:Monosaccharides / Q000138:chemical synthesis* / Q000737:chemistry; D011134:Polysaccharides / Q000737:chemistry*; D013237:Stereoisomerism; D013865:Thioglycosides / Q000032:analysis / Q000737:chemistry*
chemical_list: C569216:6-O-methyl-D-glycero-alpha-L-gluco-heptopyranose; D009005:Monosaccharides; D011134:Polysaccharides; D013865:Thioglycosides; D005990:Glycerol