Appel-reagent-mediated transformation of glycosyl hemiacetal derivatives into thioglycosides and glycosyl thiols

A series of glycosyl hemiacetal derivatives have been transformed into thioglycosides and glycosyl thiols in a one-pot two-step reaction sequence mediated by Appel reagent (carbon tetrabromide and triphenylphosphine). 1,2-trans-Thioglycosides and β-glycosyl thiol derivatives were stereoselectively f...

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Detalles Bibliográficos
Autores principales: Ghosh, Tamashree, Santra, Abhishek, Misra, Anup Kumar
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2013
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3678522/
https://www.ncbi.nlm.nih.gov/pubmed/23766814
http://dx.doi.org/10.3762/bjoc.9.112
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author Ghosh, Tamashree
Santra, Abhishek
Misra, Anup Kumar
author_facet Ghosh, Tamashree
Santra, Abhishek
Misra, Anup Kumar
author_sort Ghosh, Tamashree
collection PubMed
description A series of glycosyl hemiacetal derivatives have been transformed into thioglycosides and glycosyl thiols in a one-pot two-step reaction sequence mediated by Appel reagent (carbon tetrabromide and triphenylphosphine). 1,2-trans-Thioglycosides and β-glycosyl thiol derivatives were stereoselectively formed by the reaction of the in situ generated glycosyl bromides with thiols and sodium carbonotrithioate. The reaction conditions are reasonably simple and yields were very good.
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spelling pubmed-36785222013-06-13 Appel-reagent-mediated transformation of glycosyl hemiacetal derivatives into thioglycosides and glycosyl thiols Ghosh, Tamashree Santra, Abhishek Misra, Anup Kumar Beilstein J Org Chem Full Research Paper A series of glycosyl hemiacetal derivatives have been transformed into thioglycosides and glycosyl thiols in a one-pot two-step reaction sequence mediated by Appel reagent (carbon tetrabromide and triphenylphosphine). 1,2-trans-Thioglycosides and β-glycosyl thiol derivatives were stereoselectively formed by the reaction of the in situ generated glycosyl bromides with thiols and sodium carbonotrithioate. The reaction conditions are reasonably simple and yields were very good. Beilstein-Institut 2013-05-22 /pmc/articles/PMC3678522/ /pubmed/23766814 http://dx.doi.org/10.3762/bjoc.9.112 Text en Copyright © 2013, Ghosh 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
Ghosh, Tamashree
Santra, Abhishek
Misra, Anup Kumar
Appel-reagent-mediated transformation of glycosyl hemiacetal derivatives into thioglycosides and glycosyl thiols
title Appel-reagent-mediated transformation of glycosyl hemiacetal derivatives into thioglycosides and glycosyl thiols
title_full Appel-reagent-mediated transformation of glycosyl hemiacetal derivatives into thioglycosides and glycosyl thiols
title_fullStr Appel-reagent-mediated transformation of glycosyl hemiacetal derivatives into thioglycosides and glycosyl thiols
title_full_unstemmed Appel-reagent-mediated transformation of glycosyl hemiacetal derivatives into thioglycosides and glycosyl thiols
title_short Appel-reagent-mediated transformation of glycosyl hemiacetal derivatives into thioglycosides and glycosyl thiols
title_sort appel-reagent-mediated transformation of glycosyl hemiacetal derivatives into thioglycosides and glycosyl thiols
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3678522/
https://www.ncbi.nlm.nih.gov/pubmed/23766814
http://dx.doi.org/10.3762/bjoc.9.112
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AT misraanupkumar appelreagentmediatedtransformationofglycosylhemiacetalderivativesintothioglycosidesandglycosylthiols

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