Synthesis of <i>Salmonella enteritidis</i> Antigenic Tetrasaccharide Repeating Unit by Employing Cationic Gold(I)-Catalyzed Glycosylation Involving Glycosyl <i>N</i>-1,1-Dimethylpropargyl Carbamate Donors
Synthesis of an antigenic tetrasaccharide repeating unit of the <i>O</i>-polysaccharide of <i>Salmonella enteritidis</i> lipopolysaccharide has been accomplished. Those four monosaccharides were assembled stereoselectively by employing our recently developed cationic gold(I)-catalyzed glycosylation methodology involving various glycosyl <i>N</i>-1,1-dimethylpropargyl carbamate donors. The newly formed α-anomeric stereochemical configuration was controlled by the axial C2-OBz of the glycosyl donors via anchimeric assistance.
Authors
- Jianglong Zhu (ORCID: https://orcid.org/0000-0001-8824-2386)
- Prem Bahadur Gurung (ORCID: https://orcid.org/0000-0002-7238-837X)
- Gavin Shine
Institutions
- University of Toledo (US)
Publication Details
- Journal
- The Journal of Organic Chemistry
- Published
- 2024-08-13
- DOI
- https://doi.org/10.1021/acs.joc.4c01484
- Citations
- 1
- Primary Topic
- Carbohydrate Chemistry and Synthesis
- Type
- article
- Field-Weighted Citation Impact
- 0.25
Funders
- University of Toledo
- National Institute of General Medical Sciences