A 3,4-trans-Fused Cyclic Protecting Group Facilitates α-Selective Catalytic Synthesis of 2-Deoxyglycosides**

A practical approach has been developed to convert glucals and rhamnals into disaccharides or glycoconjugates with high α-selectivity and yields (77–97 %) using a trans-fused cyclic 3,4-O-disiloxane protecting group and TsOH⋅H(2)O (1 mol %) as a catalyst. Control of the anomeric selectivity arises f...

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Autores principales: Balmond, Edward I, Benito-Alifonso, David, Coe, Diane M, Alder, Roger W, McGarrigle, Eoghan M, Galan, M Carmen
Formato: Online Artículo Texto
Lenguaje:English
Publicado: WILEY-VCH Verlag 2014
Materias:
Communications
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4499252/
https://www.ncbi.nlm.nih.gov/pubmed/24953049
http://dx.doi.org/10.1002/anie.201403543
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author Balmond, Edward I
Benito-Alifonso, David
Coe, Diane M
Alder, Roger W
McGarrigle, Eoghan M
Galan, M Carmen
author_facet Balmond, Edward I
Benito-Alifonso, David
Coe, Diane M
Alder, Roger W
McGarrigle, Eoghan M
Galan, M Carmen
author_sort Balmond, Edward I
collection PubMed
description A practical approach has been developed to convert glucals and rhamnals into disaccharides or glycoconjugates with high α-selectivity and yields (77–97 %) using a trans-fused cyclic 3,4-O-disiloxane protecting group and TsOH⋅H(2)O (1 mol %) as a catalyst. Control of the anomeric selectivity arises from conformational locking of the intermediate oxacarbenium cation. Glucals outperform rhamnals because the C6 side-chain conformation augments the selectivity.
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spelling pubmed-44992522015-07-16 A 3,4-trans-Fused Cyclic Protecting Group Facilitates α-Selective Catalytic Synthesis of 2-Deoxyglycosides** Balmond, Edward I Benito-Alifonso, David Coe, Diane M Alder, Roger W McGarrigle, Eoghan M Galan, M Carmen Angew Chem Int Ed Engl Communications A practical approach has been developed to convert glucals and rhamnals into disaccharides or glycoconjugates with high α-selectivity and yields (77–97 %) using a trans-fused cyclic 3,4-O-disiloxane protecting group and TsOH⋅H(2)O (1 mol %) as a catalyst. Control of the anomeric selectivity arises from conformational locking of the intermediate oxacarbenium cation. Glucals outperform rhamnals because the C6 side-chain conformation augments the selectivity. WILEY-VCH Verlag 2014-07-28 2014-06-20 /pmc/articles/PMC4499252/ /pubmed/24953049 http://dx.doi.org/10.1002/anie.201403543 Text en © 2014 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. http://creativecommons.org/licenses/by/3.0/ This is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited
spellingShingle Communications
Balmond, Edward I
Benito-Alifonso, David
Coe, Diane M
Alder, Roger W
McGarrigle, Eoghan M
Galan, M Carmen
A 3,4-trans-Fused Cyclic Protecting Group Facilitates α-Selective Catalytic Synthesis of 2-Deoxyglycosides**
title A 3,4-trans-Fused Cyclic Protecting Group Facilitates α-Selective Catalytic Synthesis of 2-Deoxyglycosides**
title_full A 3,4-trans-Fused Cyclic Protecting Group Facilitates α-Selective Catalytic Synthesis of 2-Deoxyglycosides**
title_fullStr A 3,4-trans-Fused Cyclic Protecting Group Facilitates α-Selective Catalytic Synthesis of 2-Deoxyglycosides**
title_full_unstemmed A 3,4-trans-Fused Cyclic Protecting Group Facilitates α-Selective Catalytic Synthesis of 2-Deoxyglycosides**
title_short A 3,4-trans-Fused Cyclic Protecting Group Facilitates α-Selective Catalytic Synthesis of 2-Deoxyglycosides**
title_sort 3,4-trans-fused cyclic protecting group facilitates α-selective catalytic synthesis of 2-deoxyglycosides**
topic Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4499252/
https://www.ncbi.nlm.nih.gov/pubmed/24953049
http://dx.doi.org/10.1002/anie.201403543
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