864948-63-0Relevant academic research and scientific papers
Practical synthesis of (-)-1-amino-1-deoxy-myo-inositol from achiral precursors
Gonzalez-Bulnes, Patricia,Casas, Josefina,Delgado, Antonio,Llebaria, Amadeu
, p. 1947 - 1952 (2007)
A new synthesis of enantiomerically pure 1-amino-1-deoxy-myo-inositol is reported. The route described employs p-benzoquinone, 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.
On the regio- and stereoselective synthesis of aminocyclitols from cyclitol epoxides: The effect of Li as a chelating agent
Serrano, Pedro,Llebaria, Amadeu,Vazquez, Jordi,De Pablo, Joan,Anglada, Josep M.,Delgado, Antonio
, p. 4465 - 4472 (2005)
Experimental and theoretical studies on the influence of Li ions on the regio- and the stereoselectivity of the reaction of cyclitol epoxides with nitrogen nucleophiles have been carried out. Model studies with NaN3 as a nucleophile in the abse
