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.

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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

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article

Synthesis of Salmonella enteritidis Antigenic Tetrasaccharide Repeating Unit by Employing Cationic Gold(I)-Catalyzed Glycosylation Involving Glycosyl N-1,1-Dimethylpropargyl Carbamate Donors

Jianglong Zhu, Prem Bahadur Gurung, Gavin Shine
1 citations
The Journal of Organic Chemistry
Carbohydrate Chemistry and Synthesis
0.25
article

Synthesis of Salmonella enteritidis Antigenic Tetrasaccharide Repeating Unit by Employing Cationic Gold(I)-Catalyzed Glycosylation Involving Glycosyl N-1,1-Dimethylpropargyl Carbamate Donors

Jianglong Zhu, Prem Bahadur Gurung, Gavin Shine
article en
1 citations

Abstract

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.

The Journal of Organic ChemistryVol. 89(17)
University of Toledo (US)
University of Toledo, National Institute of General Medical Sciences
Openalex Percentile: Top 49%
Carbohydrate Chemistry and Synthesis
0.25
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