Electrochemical generation of 2,3-oxazolidinone glycosyl triflates as an intermediate for stereoselective glycosylation

Glycosyl triflates with a 2,3-oxazolidinone protecting group were generated from thioglycosides by low-temperature electrochemical oxidation. The glycosyl triflates reacted with alcohols to give the corresponding glycosides β-selectively at low temperatures. However, α-selectivity was observed in th...

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Detalles Bibliográficos
Autores principales: Nokami, Toshiki, Shibuya, Akito, Saigusa, Yoshihiro, Manabe, Shino, Ito, Yukishige, Yoshida, Jun-ichi
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2012
Materias:
Letter
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3326625/
https://www.ncbi.nlm.nih.gov/pubmed/22509217
http://dx.doi.org/10.3762/bjoc.8.52
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author Nokami, Toshiki
Shibuya, Akito
Saigusa, Yoshihiro
Manabe, Shino
Ito, Yukishige
Yoshida, Jun-ichi
author_facet Nokami, Toshiki
Shibuya, Akito
Saigusa, Yoshihiro
Manabe, Shino
Ito, Yukishige
Yoshida, Jun-ichi
author_sort Nokami, Toshiki
collection PubMed
description Glycosyl triflates with a 2,3-oxazolidinone protecting group were generated from thioglycosides by low-temperature electrochemical oxidation. The glycosyl triflates reacted with alcohols to give the corresponding glycosides β-selectively at low temperatures. However, α-selectivity was observed in the absence of base at elevated reaction temperatures. In situ generated triflic acid promotes the isomerization of β-products to α-products.
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spelling pubmed-33266252012-04-16 Electrochemical generation of 2,3-oxazolidinone glycosyl triflates as an intermediate for stereoselective glycosylation Nokami, Toshiki Shibuya, Akito Saigusa, Yoshihiro Manabe, Shino Ito, Yukishige Yoshida, Jun-ichi Beilstein J Org Chem Letter Glycosyl triflates with a 2,3-oxazolidinone protecting group were generated from thioglycosides by low-temperature electrochemical oxidation. The glycosyl triflates reacted with alcohols to give the corresponding glycosides β-selectively at low temperatures. However, α-selectivity was observed in the absence of base at elevated reaction temperatures. In situ generated triflic acid promotes the isomerization of β-products to α-products. Beilstein-Institut 2012-03-28 /pmc/articles/PMC3326625/ /pubmed/22509217 http://dx.doi.org/10.3762/bjoc.8.52 Text en Copyright © 2012, Nokami et al. https://creativecommons.org/licenses/by/2.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Letter
Nokami, Toshiki
Shibuya, Akito
Saigusa, Yoshihiro
Manabe, Shino
Ito, Yukishige
Yoshida, Jun-ichi
Electrochemical generation of 2,3-oxazolidinone glycosyl triflates as an intermediate for stereoselective glycosylation
title Electrochemical generation of 2,3-oxazolidinone glycosyl triflates as an intermediate for stereoselective glycosylation
title_full Electrochemical generation of 2,3-oxazolidinone glycosyl triflates as an intermediate for stereoselective glycosylation
title_fullStr Electrochemical generation of 2,3-oxazolidinone glycosyl triflates as an intermediate for stereoselective glycosylation
title_full_unstemmed Electrochemical generation of 2,3-oxazolidinone glycosyl triflates as an intermediate for stereoselective glycosylation
title_short Electrochemical generation of 2,3-oxazolidinone glycosyl triflates as an intermediate for stereoselective glycosylation
title_sort electrochemical generation of 2,3-oxazolidinone glycosyl triflates as an intermediate for stereoselective glycosylation
topic Letter
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3326625/
https://www.ncbi.nlm.nih.gov/pubmed/22509217
http://dx.doi.org/10.3762/bjoc.8.52
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