Stereoselective Glycosylation of 2-Nitrogalactals Catalyzed by a Bifunctional Organocatalyst

[Image: see text] The use of a bifunctional cinchona/thiourea organocatalyst for the direct and α-stereoselective glycosylation of 2-nitrogalactals is demonstrated for the first time. The conditions are mild, practical, and applicable to a wide range of glycoside acceptors with products being isolat...

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Autores principales: Medina, Sandra, Harper, Matthew J., Balmond, Edward I., Miranda, Silvia, Crisenza, Giacomo E. M., Coe, Diane M., McGarrigle, Eoghan M., Galan, M. Carmen
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2016
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5049936/
https://www.ncbi.nlm.nih.gov/pubmed/27529800
http://dx.doi.org/10.1021/acs.orglett.6b01962
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author Medina, Sandra
Harper, Matthew J.
Balmond, Edward I.
Miranda, Silvia
Crisenza, Giacomo E. M.
Coe, Diane M.
McGarrigle, Eoghan M.
Galan, M. Carmen
author_facet Medina, Sandra
Harper, Matthew J.
Balmond, Edward I.
Miranda, Silvia
Crisenza, Giacomo E. M.
Coe, Diane M.
McGarrigle, Eoghan M.
Galan, M. Carmen
author_sort Medina, Sandra
collection PubMed
description [Image: see text] The use of a bifunctional cinchona/thiourea organocatalyst for the direct and α-stereoselective glycosylation of 2-nitrogalactals is demonstrated for the first time. The conditions are mild, practical, and applicable to a wide range of glycoside acceptors with products being isolated in good to excellent yields. The method is exemplified in the synthesis of mucin type Core 6 and 7 glycopeptides.
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spelling pubmed-50499362016-10-05 Stereoselective Glycosylation of 2-Nitrogalactals Catalyzed by a Bifunctional Organocatalyst Medina, Sandra Harper, Matthew J. Balmond, Edward I. Miranda, Silvia Crisenza, Giacomo E. M. Coe, Diane M. McGarrigle, Eoghan M. Galan, M. Carmen Org Lett [Image: see text] The use of a bifunctional cinchona/thiourea organocatalyst for the direct and α-stereoselective glycosylation of 2-nitrogalactals is demonstrated for the first time. The conditions are mild, practical, and applicable to a wide range of glycoside acceptors with products being isolated in good to excellent yields. The method is exemplified in the synthesis of mucin type Core 6 and 7 glycopeptides. American Chemical Society 2016-08-16 2016-09-02 /pmc/articles/PMC5049936/ /pubmed/27529800 http://dx.doi.org/10.1021/acs.orglett.6b01962 Text en Copyright © 2016 American Chemical Society This is an open access article published under a Creative Commons Attribution (CC-BY) License (http://pubs.acs.org/page/policy/authorchoice_ccby_termsofuse.html) , which permits unrestricted use, distribution and reproduction in any medium, provided the author and source are cited.
spellingShingle Medina, Sandra
Harper, Matthew J.
Balmond, Edward I.
Miranda, Silvia
Crisenza, Giacomo E. M.
Coe, Diane M.
McGarrigle, Eoghan M.
Galan, M. Carmen
Stereoselective Glycosylation of 2-Nitrogalactals Catalyzed by a Bifunctional Organocatalyst
title Stereoselective Glycosylation of 2-Nitrogalactals Catalyzed by a Bifunctional Organocatalyst
title_full Stereoselective Glycosylation of 2-Nitrogalactals Catalyzed by a Bifunctional Organocatalyst
title_fullStr Stereoselective Glycosylation of 2-Nitrogalactals Catalyzed by a Bifunctional Organocatalyst
title_full_unstemmed Stereoselective Glycosylation of 2-Nitrogalactals Catalyzed by a Bifunctional Organocatalyst
title_short Stereoselective Glycosylation of 2-Nitrogalactals Catalyzed by a Bifunctional Organocatalyst
title_sort stereoselective glycosylation of 2-nitrogalactals catalyzed by a bifunctional organocatalyst
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5049936/
https://www.ncbi.nlm.nih.gov/pubmed/27529800
http://dx.doi.org/10.1021/acs.orglett.6b01962
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