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Straightforward synthesis of the hexasaccharide repeating unit of the O-specific polysaccharide of Salmonella arizonae O62.
- Source :
-
Glycoconjugate journal [Glycoconj J] 2023 Aug; Vol. 40 (4), pp. 449-459. Date of Electronic Publication: 2023 May 23. - Publication Year :
- 2023
-
Abstract
- A straightforward synthesis of the hexasaccharide repeating unit of the O-specific polysaccharide of Salmonella arizonae O62 was achieved in very good yield applying sequential glycosylation strategy. Successful regioselective glycosylation of the di-hydroxylated L-rhamnose moiety allowed achieving the desired compound in minimum number of synthetic steps. TEMPO catalyzed and [bis(acetoxy)iodo]benzene (BAIB) mediated late stage regioselective oxidation of a primary hydroxyl group into carboxylic acid was achieved in the hexasaccharide derivative. The glycosylation steps were high yielding with high stereochemical outcome. The desired hexasaccharide was obtained in 7% over all yield in fourteen steps starting from suitably functionalized monosaccharide intermediates.<br /> (© 2023. The Author(s), under exclusive licence to Springer Science+Business Media, LLC, part of Springer Nature.)
Details
- Language :
- English
- ISSN :
- 1573-4986
- Volume :
- 40
- Issue :
- 4
- Database :
- MEDLINE
- Journal :
- Glycoconjugate journal
- Publication Type :
- Academic Journal
- Accession number :
- 37219745
- Full Text :
- https://doi.org/10.1007/s10719-023-10122-x