TMSBr-mediated solvent- and work-up-free synthesis of α-2-deoxyglycosides from glycals

The thio-additions of glycals were efficiently promoted by a stoichiometric amount of trimethylsilyl bromide (TMSBr) to produce S-2-deoxyglycosides under solvent-free conditions in good to excellent yields. In addition, with triphenylphosphine oxide as an additive, the TMSBr-mediated direct glycosyl...

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Autores principales: Hsu, Mei-Yuan, Liu, Yi-Pei, Lam, Sarah, Lin, Su-Ching, Wang, Cheng-Chung
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2016
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4979735/
https://www.ncbi.nlm.nih.gov/pubmed/27559420
http://dx.doi.org/10.3762/bjoc.12.164
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author Hsu, Mei-Yuan
Liu, Yi-Pei
Lam, Sarah
Lin, Su-Ching
Wang, Cheng-Chung
author_facet Hsu, Mei-Yuan
Liu, Yi-Pei
Lam, Sarah
Lin, Su-Ching
Wang, Cheng-Chung
author_sort Hsu, Mei-Yuan
collection PubMed
description The thio-additions of glycals were efficiently promoted by a stoichiometric amount of trimethylsilyl bromide (TMSBr) to produce S-2-deoxyglycosides under solvent-free conditions in good to excellent yields. In addition, with triphenylphosphine oxide as an additive, the TMSBr-mediated direct glycosylations of glycals with a large range of alcohols were highly α-selective.
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spelling pubmed-49797352016-08-24 TMSBr-mediated solvent- and work-up-free synthesis of α-2-deoxyglycosides from glycals Hsu, Mei-Yuan Liu, Yi-Pei Lam, Sarah Lin, Su-Ching Wang, Cheng-Chung Beilstein J Org Chem Full Research Paper The thio-additions of glycals were efficiently promoted by a stoichiometric amount of trimethylsilyl bromide (TMSBr) to produce S-2-deoxyglycosides under solvent-free conditions in good to excellent yields. In addition, with triphenylphosphine oxide as an additive, the TMSBr-mediated direct glycosylations of glycals with a large range of alcohols were highly α-selective. Beilstein-Institut 2016-08-04 /pmc/articles/PMC4979735/ /pubmed/27559420 http://dx.doi.org/10.3762/bjoc.12.164 Text en Copyright © 2016, Hsu 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 Full Research Paper
Hsu, Mei-Yuan
Liu, Yi-Pei
Lam, Sarah
Lin, Su-Ching
Wang, Cheng-Chung
TMSBr-mediated solvent- and work-up-free synthesis of α-2-deoxyglycosides from glycals
title TMSBr-mediated solvent- and work-up-free synthesis of α-2-deoxyglycosides from glycals
title_full TMSBr-mediated solvent- and work-up-free synthesis of α-2-deoxyglycosides from glycals
title_fullStr TMSBr-mediated solvent- and work-up-free synthesis of α-2-deoxyglycosides from glycals
title_full_unstemmed TMSBr-mediated solvent- and work-up-free synthesis of α-2-deoxyglycosides from glycals
title_short TMSBr-mediated solvent- and work-up-free synthesis of α-2-deoxyglycosides from glycals
title_sort tmsbr-mediated solvent- and work-up-free synthesis of α-2-deoxyglycosides from glycals
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4979735/
https://www.ncbi.nlm.nih.gov/pubmed/27559420
http://dx.doi.org/10.3762/bjoc.12.164
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