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Abstract:

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.

Registro:

Documento: Artículo
Título:Usage of α-picoline borane for the reductive amination of carbohydrates
Autor:Cosenza, V.A.; Navarro, D.A.; Stortz, C.A.
Filiación:Departamento de Química Orgánica-Cihidecar, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Ciudad Universitaria, 3er piso, 1428 Buenos Aires, Argentina
Palabras clave:Amadori rearrangement; Carbohydrates; Picoline borane; Reductive Amination
Año:2011
Volumen:2011
Número:7
Página de inicio:182
Página de fin:194
DOI: http://dx.doi.org/10.3998/ark.5550190.0012.716
Título revista:Arkivoc
Título revista abreviado:Arkivoc
ISSN:1551-701
CODEN:AGFUA
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_1551-701_v2011_n7_p182_Cosenza

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Citas:

---------- APA ----------
Cosenza, V.A., Navarro, D.A. & Stortz, C.A. (2011) . Usage of α-picoline borane for the reductive amination of carbohydrates. Arkivoc, 2011(7), 182-194.
http://dx.doi.org/10.3998/ark.5550190.0012.716
---------- CHICAGO ----------
Cosenza, V.A., Navarro, D.A., Stortz, C.A. "Usage of α-picoline borane for the reductive amination of carbohydrates" . Arkivoc 2011, no. 7 (2011) : 182-194.
http://dx.doi.org/10.3998/ark.5550190.0012.716
---------- MLA ----------
Cosenza, V.A., Navarro, D.A., Stortz, C.A. "Usage of α-picoline borane for the reductive amination of carbohydrates" . Arkivoc, vol. 2011, no. 7, 2011, pp. 182-194.
http://dx.doi.org/10.3998/ark.5550190.0012.716
---------- VANCOUVER ----------
Cosenza, V.A., Navarro, D.A., Stortz, C.A. Usage of α-picoline borane for the reductive amination of carbohydrates. Arkivoc. 2011;2011(7):182-194.
http://dx.doi.org/10.3998/ark.5550190.0012.716