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Título: | Practical synthesis of (-)-1-amino-1-deoxy-myo-inositol from achiral precursors |
Autor: | González-Bulnes, Patricia CSIC; Casas, Josefina CSIC ORCID ; Delgado Cirilo, Antonio CSIC ORCID; Llebaria, Amadeu CSIC ORCID | Palabras clave: | Aminoinositol Conduritol B Myo-Inositol Aminoconduritol Enantiomer Kinetic resolution |
Fecha de publicación: | 5-may-2007 | Editor: | Elsevier | Citación: | Carbohidrate Research 342(12-13): 1947-1952 (2007) | Resumen: | A new synthesis of enantiomerically pure 1-amino-1-deoxy-myo-inositol is reported. The route described employs pbenzoquinone, an achiral compound, as the starting material to give conduritol B tetraacetate in three steps. Kinetic resolution of this compound using a palladium catalyst with a chiral ligand allows access to a conduritol B tetraester in high enantiomeric excess. This compound is transformed into tetrabenzyl conduritol B epoxide, which is regioselectively opened with azide to give the key azidocyclitol. Final transformation into (-)-1-amino-1-deoxy-myo-inositol hydrochloride is achieved in four synthetic steps. This sequence allows the synthesis of this compound in high enantiomeric purity in a semi-preparative scale. | Descripción: | 6 pages, 3 schemes.-- PMID: 17524374 [PubMed].-- Printed version published on Sep 3, 2007. | Versión del editor: | http://dx.doi.org/10.1016/j.carres.2007.04.024 | URI: | http://hdl.handle.net/10261/9509 | DOI: | 10.1016/j.carres.2007.04.024 | ISSN: | 0008-6215 |
Aparece en las colecciones: | (IQAC) Artículos |
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