Benzyne arylation of oxathiane glycosyl donors

The arylation of bicyclic oxathiane glycosyl donors has been achieved using benzyne generated in situ from 1-aminobenzotriazole (1-ABT) and lead tetraacetate. Following sulfur arylation, glycosylation of acetate ions proceeded with high levels of stereoselectivity to afford α-glycosyl acetates in a...

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Detalles Bibliográficos
Autores principales: Fascione, Martin A, Turnbull, W Bruce
Formato: Texto
Lenguaje:English
Publicado: Beilstein-Institut 2010
Materias:
Preliminary Communication
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2870982/
https://www.ncbi.nlm.nih.gov/pubmed/20485601
http://dx.doi.org/10.3762/bjoc.6.19
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author Fascione, Martin A
Turnbull, W Bruce
author_facet Fascione, Martin A
Turnbull, W Bruce
author_sort Fascione, Martin A
collection PubMed
description The arylation of bicyclic oxathiane glycosyl donors has been achieved using benzyne generated in situ from 1-aminobenzotriazole (1-ABT) and lead tetraacetate. Following sulfur arylation, glycosylation of acetate ions proceeded with high levels of stereoselectivity to afford α-glycosyl acetates in a ‘one-pot’ reaction, even in the presence of alternative acceptor alcohols.
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spelling pubmed-28709822010-05-18 Benzyne arylation of oxathiane glycosyl donors Fascione, Martin A Turnbull, W Bruce Beilstein J Org Chem Preliminary Communication The arylation of bicyclic oxathiane glycosyl donors has been achieved using benzyne generated in situ from 1-aminobenzotriazole (1-ABT) and lead tetraacetate. Following sulfur arylation, glycosylation of acetate ions proceeded with high levels of stereoselectivity to afford α-glycosyl acetates in a ‘one-pot’ reaction, even in the presence of alternative acceptor alcohols. Beilstein-Institut 2010-02-22 /pmc/articles/PMC2870982/ /pubmed/20485601 http://dx.doi.org/10.3762/bjoc.6.19 Text en Copyright © 2010, Fascione and Turnbull 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 Preliminary Communication
Fascione, Martin A
Turnbull, W Bruce
Benzyne arylation of oxathiane glycosyl donors
title Benzyne arylation of oxathiane glycosyl donors
title_full Benzyne arylation of oxathiane glycosyl donors
title_fullStr Benzyne arylation of oxathiane glycosyl donors
title_full_unstemmed Benzyne arylation of oxathiane glycosyl donors
title_short Benzyne arylation of oxathiane glycosyl donors
title_sort benzyne arylation of oxathiane glycosyl donors
topic Preliminary Communication
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2870982/
https://www.ncbi.nlm.nih.gov/pubmed/20485601
http://dx.doi.org/10.3762/bjoc.6.19
work_keys_str_mv AT fascionemartina benzynearylationofoxathianeglycosyldonors
AT turnbullwbruce benzynearylationofoxathianeglycosyldonors

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