Synthesis of Benzyl 2-Deoxy-C-Glycosides

[Image: see text] A synthetic method for benzyl 2-deoxy-C-glycosides has been developed. Palladium-catalyzed benzyl C-glycosylation of TIPS-protected 1-tributylstannyl glycals with a variety of benzyl bromides provided protected benzyl C-glycals. In this reaction, the use of PdCl(2)(dppe) promoted a...

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Autor principal: Shinozuka, Tsuyoshi
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2020
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7774260/
https://www.ncbi.nlm.nih.gov/pubmed/33403281
http://dx.doi.org/10.1021/acsomega.0c04874
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author Shinozuka, Tsuyoshi
author_facet Shinozuka, Tsuyoshi
author_sort Shinozuka, Tsuyoshi
collection PubMed
description [Image: see text] A synthetic method for benzyl 2-deoxy-C-glycosides has been developed. Palladium-catalyzed benzyl C-glycosylation of TIPS-protected 1-tributylstannyl glycals with a variety of benzyl bromides provided protected benzyl C-glycals. In this reaction, the use of PdCl(2)(dppe) promoted a clean reaction, whereas the reaction was accelerated by the addition of Na(2)CO(3). The subsequent transformations provided a novel class of benzyl 2-deoxy-C-glycosides.
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spelling pubmed-77742602021-01-04 Synthesis of Benzyl 2-Deoxy-C-Glycosides Shinozuka, Tsuyoshi ACS Omega [Image: see text] A synthetic method for benzyl 2-deoxy-C-glycosides has been developed. Palladium-catalyzed benzyl C-glycosylation of TIPS-protected 1-tributylstannyl glycals with a variety of benzyl bromides provided protected benzyl C-glycals. In this reaction, the use of PdCl(2)(dppe) promoted a clean reaction, whereas the reaction was accelerated by the addition of Na(2)CO(3). The subsequent transformations provided a novel class of benzyl 2-deoxy-C-glycosides. American Chemical Society 2020-12-17 /pmc/articles/PMC7774260/ /pubmed/33403281 http://dx.doi.org/10.1021/acsomega.0c04874 Text en © 2020 American Chemical Society This is an open access article published under a Creative Commons Non-Commercial No Derivative Works (CC-BY-NC-ND) Attribution License (http://pubs.acs.org/page/policy/authorchoice_ccbyncnd_termsofuse.html) , which permits copying and redistribution of the article, and creation of adaptations, all for non-commercial purposes.
spellingShingle Shinozuka, Tsuyoshi
Synthesis of Benzyl 2-Deoxy-C-Glycosides
title Synthesis of Benzyl 2-Deoxy-C-Glycosides
title_full Synthesis of Benzyl 2-Deoxy-C-Glycosides
title_fullStr Synthesis of Benzyl 2-Deoxy-C-Glycosides
title_full_unstemmed Synthesis of Benzyl 2-Deoxy-C-Glycosides
title_short Synthesis of Benzyl 2-Deoxy-C-Glycosides
title_sort synthesis of benzyl 2-deoxy-c-glycosides
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7774260/
https://www.ncbi.nlm.nih.gov/pubmed/33403281
http://dx.doi.org/10.1021/acsomega.0c04874
work_keys_str_mv AT shinozukatsuyoshi synthesisofbenzyl2deoxycglycosides

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