Benzyne-Promoted, 1,2-cis-Selective O-Glycosylation with Benzylchalcogenoglycoside Donors

[Image: see text] Here, we show that the reaction of benzylchalcogenoglycosides with benzyne in the presence of alcohols results in highly 1,2-cis-selective O-glycosylation in a solvent-dependent manner. Thioglycosides, selenoglycosides, and alcohols with a range of nucleophilicities lead to a produ...

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Autores principales: Duong, Tiffany, Valenzuela, Erik Alvarez, Ragains, Justin R.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2023
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10696609/
https://www.ncbi.nlm.nih.gov/pubmed/37970840
http://dx.doi.org/10.1021/acs.orglett.3c03502
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author Duong, Tiffany
Valenzuela, Erik Alvarez
Ragains, Justin R.
author_facet Duong, Tiffany
Valenzuela, Erik Alvarez
Ragains, Justin R.
author_sort Duong, Tiffany
collection PubMed
description [Image: see text] Here, we show that the reaction of benzylchalcogenoglycosides with benzyne in the presence of alcohols results in highly 1,2-cis-selective O-glycosylation in a solvent-dependent manner. Thioglycosides, selenoglycosides, and alcohols with a range of nucleophilicities lead to a productive reaction, and unusual protecting groups, auxiliary groups, and additives are avoided.
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spelling pubmed-106966092023-12-06 Benzyne-Promoted, 1,2-cis-Selective O-Glycosylation with Benzylchalcogenoglycoside Donors Duong, Tiffany Valenzuela, Erik Alvarez Ragains, Justin R. Org Lett [Image: see text] Here, we show that the reaction of benzylchalcogenoglycosides with benzyne in the presence of alcohols results in highly 1,2-cis-selective O-glycosylation in a solvent-dependent manner. Thioglycosides, selenoglycosides, and alcohols with a range of nucleophilicities lead to a productive reaction, and unusual protecting groups, auxiliary groups, and additives are avoided. American Chemical Society 2023-11-16 /pmc/articles/PMC10696609/ /pubmed/37970840 http://dx.doi.org/10.1021/acs.orglett.3c03502 Text en © 2023 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Duong, Tiffany
Valenzuela, Erik Alvarez
Ragains, Justin R.
Benzyne-Promoted, 1,2-cis-Selective O-Glycosylation with Benzylchalcogenoglycoside Donors
title Benzyne-Promoted, 1,2-cis-Selective O-Glycosylation with Benzylchalcogenoglycoside Donors
title_full Benzyne-Promoted, 1,2-cis-Selective O-Glycosylation with Benzylchalcogenoglycoside Donors
title_fullStr Benzyne-Promoted, 1,2-cis-Selective O-Glycosylation with Benzylchalcogenoglycoside Donors
title_full_unstemmed Benzyne-Promoted, 1,2-cis-Selective O-Glycosylation with Benzylchalcogenoglycoside Donors
title_short Benzyne-Promoted, 1,2-cis-Selective O-Glycosylation with Benzylchalcogenoglycoside Donors
title_sort benzyne-promoted, 1,2-cis-selective o-glycosylation with benzylchalcogenoglycoside donors
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10696609/
https://www.ncbi.nlm.nih.gov/pubmed/37970840
http://dx.doi.org/10.1021/acs.orglett.3c03502
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AT valenzuelaerikalvarez benzynepromoted12cisselectiveoglycosylationwithbenzylchalcogenoglycosidedonors
AT ragainsjustinr benzynepromoted12cisselectiveoglycosylationwithbenzylchalcogenoglycosidedonors

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