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...
Guardado en:
| Autores principales: | , , |
|---|---|
| Formato: | JOUR |
| Materias: | |
| Acceso en línea: | http://hdl.handle.net/20.500.12110/paper_1551-701_v2011_n7_p182_Cosenza |
| Aporte de: |
| id |
todo:paper_1551-701_v2011_n7_p182_Cosenza |
|---|---|
| record_format |
dspace |
| spelling |
todo:paper_1551-701_v2011_n7_p182_Cosenza2023-10-03T16:25:19Z Usage of α-picoline borane for the reductive amination of carbohydrates Cosenza, V.A. Navarro, D.A. Stortz, C.A. 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. JOUR info:eu-repo/semantics/openAccess http://creativecommons.org/licenses/by/2.5/ar 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 Cosenza, V.A. Navarro, D.A. Stortz, C.A. 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. |
| format |
JOUR |
| author |
Cosenza, V.A. Navarro, D.A. Stortz, C.A. |
| author_facet |
Cosenza, V.A. Navarro, D.A. Stortz, C.A. |
| author_sort |
Cosenza, V.A. |
| 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 |
| url |
http://hdl.handle.net/20.500.12110/paper_1551-701_v2011_n7_p182_Cosenza |
| work_keys_str_mv |
AT cosenzava usageofapicolineboraneforthereductiveaminationofcarbohydrates AT navarroda usageofapicolineboraneforthereductiveaminationofcarbohydrates AT stortzca usageofapicolineboraneforthereductiveaminationofcarbohydrates |
| _version_ |
1782025988209639424 |