Expedient synthesis of 1,6-anhydro-α-D-galactofuranose, a useful intermediate for glycobiological tools

A new and efficient three-step procedure for the synthesis of 1,6-anhydro-α-D-galactofuranose is described. The key step involves the formation of the galactofuranosyl iodide by treatment of per-O-TBS-D-Galf with TMSI, the selective 6-O-desilylation by an excess of TMSI, and the simultaneous nucleop...

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Detalles Bibliográficos
Autores principales: Baldoni, Luciana, Marino, Carla
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2014
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4143087/
https://www.ncbi.nlm.nih.gov/pubmed/25161723
http://dx.doi.org/10.3762/bjoc.10.172
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author Baldoni, Luciana
Marino, Carla
author_facet Baldoni, Luciana
Marino, Carla
author_sort Baldoni, Luciana
collection PubMed
description A new and efficient three-step procedure for the synthesis of 1,6-anhydro-α-D-galactofuranose is described. The key step involves the formation of the galactofuranosyl iodide by treatment of per-O-TBS-D-Galf with TMSI, the selective 6-O-desilylation by an excess of TMSI, and the simultaneous nucleophilic attack of the 6-hydroxy group on the anomeric carbon, with the iodide as a good leaving group. This compound is a good precursor for building blocks for the construction of 1→6 linkages.
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spelling pubmed-41430872014-08-26 Expedient synthesis of 1,6-anhydro-α-D-galactofuranose, a useful intermediate for glycobiological tools Baldoni, Luciana Marino, Carla Beilstein J Org Chem Full Research Paper A new and efficient three-step procedure for the synthesis of 1,6-anhydro-α-D-galactofuranose is described. The key step involves the formation of the galactofuranosyl iodide by treatment of per-O-TBS-D-Galf with TMSI, the selective 6-O-desilylation by an excess of TMSI, and the simultaneous nucleophilic attack of the 6-hydroxy group on the anomeric carbon, with the iodide as a good leaving group. This compound is a good precursor for building blocks for the construction of 1→6 linkages. Beilstein-Institut 2014-07-21 /pmc/articles/PMC4143087/ /pubmed/25161723 http://dx.doi.org/10.3762/bjoc.10.172 Text en Copyright © 2014, Baldoni and Marino 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
Baldoni, Luciana
Marino, Carla
Expedient synthesis of 1,6-anhydro-α-D-galactofuranose, a useful intermediate for glycobiological tools
title Expedient synthesis of 1,6-anhydro-α-D-galactofuranose, a useful intermediate for glycobiological tools
title_full Expedient synthesis of 1,6-anhydro-α-D-galactofuranose, a useful intermediate for glycobiological tools
title_fullStr Expedient synthesis of 1,6-anhydro-α-D-galactofuranose, a useful intermediate for glycobiological tools
title_full_unstemmed Expedient synthesis of 1,6-anhydro-α-D-galactofuranose, a useful intermediate for glycobiological tools
title_short Expedient synthesis of 1,6-anhydro-α-D-galactofuranose, a useful intermediate for glycobiological tools
title_sort expedient synthesis of 1,6-anhydro-α-d-galactofuranose, a useful intermediate for glycobiological tools
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4143087/
https://www.ncbi.nlm.nih.gov/pubmed/25161723
http://dx.doi.org/10.3762/bjoc.10.172
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