English   español  
Please use this identifier to cite or link to this item: http://hdl.handle.net/10261/9509
logo share SHARE logo core CORE   Add this article to your Mendeley library MendeleyBASE

Visualizar otros formatos: MARC | Dublin Core | RDF | ORE | MODS | METS | DIDL | DATACITE
Exportar a otros formatos:


Practical synthesis of (-)-1-amino-1-deoxy-myo-inositol from achiral precursors

AuthorsGonzález-Bulnes, Patricia ; Casas, Josefina ; Delgado Cirilo, Antonio ; Llebaria, Amadeu
Conduritol B
Kinetic resolution
Issue Date5-May-2007
CitationCarbohidrate Research 342(12-13): 1947-1952 (2007)
AbstractA 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.
Description6 pages, 3 schemes.-- PMID: 17524374 [PubMed].-- Printed version published on Sep 3, 2007.
Publisher version (URL)http://dx.doi.org/10.1016/j.carres.2007.04.024
Appears in Collections:(IQAC) Artículos
Files in This Item:
There are no files associated with this item.
Show full item record
Review this work

Related articles:

WARNING: Items in Digital.CSIC are protected by copyright, with all rights reserved, unless otherwise indicated.