Stereoselective Synthesis of 2-Azido-2-deoxy-β-d-mannosides via Cs
Journal
The Journal of organic chemistry
ISSN: 1520-6904
Titre abrégé: J Org Chem
Pays: United States
ID NLM: 2985193R
Informations de publication
Date de publication:
18 12 2020
18 12 2020
Historique:
pubmed:
18
11
2020
medline:
24
6
2021
entrez:
17
11
2020
Statut:
ppublish
Résumé
Cesium carbonate-mediated anomeric O-alkylation of various protected 2-azido-2-deoxy-d-mannoses with primary triflate electrophiles afforded corresponding 2-azido-2-deoxy-β-mannosides in good yields and excellent anomeric selectivity. In addition, 1,3-dibromo-5,5-dimethylhydantoin was found to be the optimal oxidant for preparation of those 2-azido-2-deoxy-d-mannoses from their corresponding thioglycosides. The utilization of this method was demonstrated in the synthesis of a tetrasaccharide fragment of
Identifiants
pubmed: 33201716
doi: 10.1021/acs.joc.0c02370
pmc: PMC7799176
mid: NIHMS1656720
doi:
Substances chimiques
Mannosides
0
Oligosaccharides
0
Uronic Acids
0
teichuronic acid
37251-79-9
Types de publication
Journal Article
Research Support, N.I.H., Extramural
Research Support, Non-U.S. Gov't
Langues
eng
Sous-ensembles de citation
IM
Pagination
16196-16206Subventions
Organisme : NIGMS NIH HHS
ID : U01 GM125289
Pays : United States
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