title: Synthesis of a tetrasaccharide analog corresponding to the repeating unit of the O-polysaccharide of Salmonella enterica O59: unexpected stereo outcome in glycosylation.
abstract: Convergent synthesis of a tetrasaccharide analog corresponding to the repeating unit of the O-polysaccharide of Salmonella enterica O59 is presented. A thioglycoside disaccharide donor was prepared by the glycosylation of two thioglycosides by tuning their relative reactivity. An unexpected stereochemical outcome was observed in a glycosylation using an ethyl 2-O-acetyl-3-O-benzyl-4,6-O-bensylidene-thio-galactoside donor, where the alpha-galactoside was formed in spite of the presence of the 2-O-acetyl participating group.
authors.affiliation: Bose Institute, Division of Molecular Medicine, P-1/12, C.I.T. Scheme VII M, Kolkata 700054, India.
authors.forename: Abhijit
authors.initials: A
authors.lastname: Sau
authors.forename: Rajib
authors.initials: R
authors.lastname: Panchadhayee
authors.forename: Debjani
authors.initials: D
authors.lastname: Ghosh
authors.forename: Anup Kumar
authors.initials: AK
authors.lastname: Misra
mesh_terms: D002240:Carbohydrate Sequence; D060326:Chemistry Techniques, Synthetic / Q000379:methods*; D006031:Glycosylation; D008969:Molecular Sequence Data; D019081:O Antigens / Q000737:chemistry*; D009844:Oligosaccharides / Q000138:chemical synthesis* / Q000737:chemistry*; D019779:Salmonella enterica / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D019081:O Antigens; D009844:Oligosaccharides