Expedient synthesis of 1,6-anhydro-á-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, L., Marino, C.
Formato: JOUR
Materias:
1,6-anhydro-α-D-Galf
Galactofuranosyl iodide
Galactofuranosyl precursor
Per-tert-butyldimethylsilyl-β-D-galactofuranose
Acceso en línea:http://hdl.handle.net/20.500.12110/paper_18605397_v10_n_p1651_Baldoni
Aporte de:
Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) de Universidad de Buenos Aires
id todo:paper_18605397_v10_n_p1651_Baldoni
record_format dspace
spelling todo:paper_18605397_v10_n_p1651_Baldoni2023-10-03T16:33:17Z Expedient synthesis of 1,6-anhydro-á-D-galactofuranose, a useful intermediate for glycobiological tools Baldoni, L. Marino, C. 1,6-anhydro-α-D-Galf Galactofuranosyl iodide Galactofuranosyl precursor Per-tert-butyldimethylsilyl-β-D-galactofuranose 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. © 2014 Baldoni and Marino. Fil:Baldoni, L. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. JOUR info:eu-repo/semantics/openAccess http://creativecommons.org/licenses/by/2.5/ar http://hdl.handle.net/20.500.12110/paper_18605397_v10_n_p1651_Baldoni
institution Universidad de Buenos Aires
institution_str I-28
repository_str R-134
collection Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA)
topic 1,6-anhydro-α-D-Galf
Galactofuranosyl iodide
Galactofuranosyl precursor
Per-tert-butyldimethylsilyl-β-D-galactofuranose
spellingShingle 1,6-anhydro-α-D-Galf
Galactofuranosyl iodide
Galactofuranosyl precursor
Per-tert-butyldimethylsilyl-β-D-galactofuranose
Baldoni, L.
Marino, C.
Expedient synthesis of 1,6-anhydro-á-D-galactofuranose, a useful intermediate for glycobiological tools
topic_facet 1,6-anhydro-α-D-Galf
Galactofuranosyl iodide
Galactofuranosyl precursor
Per-tert-butyldimethylsilyl-β-D-galactofuranose
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. © 2014 Baldoni and Marino.
format JOUR
author Baldoni, L.
Marino, C.
author_facet Baldoni, L.
Marino, C.
author_sort Baldoni, L.
title Expedient synthesis of 1,6-anhydro-á-D-galactofuranose, a useful intermediate for glycobiological tools
title_short Expedient synthesis of 1,6-anhydro-á-D-galactofuranose, a useful intermediate for glycobiological tools
title_full Expedient synthesis of 1,6-anhydro-á-D-galactofuranose, a useful intermediate for glycobiological tools
title_fullStr Expedient synthesis of 1,6-anhydro-á-D-galactofuranose, a useful intermediate for glycobiological tools
title_full_unstemmed Expedient synthesis of 1,6-anhydro-á-D-galactofuranose, a useful intermediate for glycobiological tools
title_sort expedient synthesis of 1,6-anhydro-á-d-galactofuranose, a useful intermediate for glycobiological tools
url http://hdl.handle.net/20.500.12110/paper_18605397_v10_n_p1651_Baldoni
work_keys_str_mv AT baldonil expedientsynthesisof16anhydroadgalactofuranoseausefulintermediateforglycobiologicaltools
AT marinoc expedientsynthesisof16anhydroadgalactofuranoseausefulintermediateforglycobiologicaltools
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