Usage of α-picoline borane for the reductive amination of carbohydrates

The reaction of reductive amination, widely used for carbohydrates, was reviewed in our lab, especially in the context of the analytical determination of carbohydrate enantiomers. The best conditions for the technique have been evaluated, showing that under optimal working conditions it is possible...

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Autores principales: Navarro, Diego Alberto, Stortz, Carlos Arturo
Publicado: 2011
Materias:
Amadori rearrangement
Carbohydrates
Picoline borane
Reductive Amination
Acceso en línea:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_1551-701_v2011_n7_p182_Cosenza
http://hdl.handle.net/20.500.12110/paper_1551-701_v2011_n7_p182_Cosenza
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Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) de Universidad de Buenos Aires
id paper:paper_1551-701_v2011_n7_p182_Cosenza
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spelling paper:paper_1551-701_v2011_n7_p182_Cosenza2023-06-08T16:23:02Z Usage of α-picoline borane for the reductive amination of carbohydrates Navarro, Diego Alberto Stortz, Carlos Arturo Amadori rearrangement Carbohydrates Picoline borane Reductive Amination The reaction of reductive amination, widely used for carbohydrates, was reviewed in our lab, especially in the context of the analytical determination of carbohydrate enantiomers. The best conditions for the technique have been evaluated, showing that under optimal working conditions it is possible to use α-picoline borane as a reducing agent instead of sodium cyanoborohydride without affecting the selectivity or the yield. The main reason for the variation of the technique was that, in the presence of acetic acid, secondary epimeric products were produced with α-picoline borane due to an Amadori rearrangement. This new modification assures lower toxicity, and thus a more environmental-friendly reaction system. Preparative scale synthesis can also be efficiently made with this reducing reagent. © ARKAT-USA, Inc. Fil:Navarro, D.A. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Stortz, C.A. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. 2011 https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_1551-701_v2011_n7_p182_Cosenza http://hdl.handle.net/20.500.12110/paper_1551-701_v2011_n7_p182_Cosenza
institution Universidad de Buenos Aires
institution_str I-28
repository_str R-134
collection Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA)
topic Amadori rearrangement
Carbohydrates
Picoline borane
Reductive Amination
spellingShingle Amadori rearrangement
Carbohydrates
Picoline borane
Reductive Amination
Navarro, Diego Alberto
Stortz, Carlos Arturo
Usage of α-picoline borane for the reductive amination of carbohydrates
topic_facet Amadori rearrangement
Carbohydrates
Picoline borane
Reductive Amination
description The reaction of reductive amination, widely used for carbohydrates, was reviewed in our lab, especially in the context of the analytical determination of carbohydrate enantiomers. The best conditions for the technique have been evaluated, showing that under optimal working conditions it is possible to use α-picoline borane as a reducing agent instead of sodium cyanoborohydride without affecting the selectivity or the yield. The main reason for the variation of the technique was that, in the presence of acetic acid, secondary epimeric products were produced with α-picoline borane due to an Amadori rearrangement. This new modification assures lower toxicity, and thus a more environmental-friendly reaction system. Preparative scale synthesis can also be efficiently made with this reducing reagent. © ARKAT-USA, Inc.
author Navarro, Diego Alberto
Stortz, Carlos Arturo
author_facet Navarro, Diego Alberto
Stortz, Carlos Arturo
author_sort Navarro, Diego Alberto
title Usage of α-picoline borane for the reductive amination of carbohydrates
title_short Usage of α-picoline borane for the reductive amination of carbohydrates
title_full Usage of α-picoline borane for the reductive amination of carbohydrates
title_fullStr Usage of α-picoline borane for the reductive amination of carbohydrates
title_full_unstemmed Usage of α-picoline borane for the reductive amination of carbohydrates
title_sort usage of α-picoline borane for the reductive amination of carbohydrates
publishDate 2011
url https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_1551-701_v2011_n7_p182_Cosenza
http://hdl.handle.net/20.500.12110/paper_1551-701_v2011_n7_p182_Cosenza
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AT stortzcarlosarturo usageofapicolineboraneforthereductiveaminationofcarbohydrates
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