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Carbohydrate Research
Article . 2007 . Peer-reviewed
License: Elsevier TDM
Data sources: Crossref
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Practical synthesis of (−)-1-amino-1-deoxy-myo-inositol from achiral precursors

Authors: González-Bulnes, Patricia; Casas, Josefina; Delgado Cirilo, Antonio; Llebaria, Amadeu;

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

Abstract

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.

Keywords

Models, Molecular, Aminoinositol, Enantiomer, Conduritol B, Kinetic resolution, Molecular Conformation, Myo-Inositol, Indicators and Reagents, Inositol, Aminoconduritol

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selected citations
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This is an alternative to the "Influence" indicator, which also reflects the overall/total impact of an article in the research community at large, based on the underlying citation network (diachronically).
BIP!Citations provided by BIP!
popularity
This indicator reflects the "current" impact/attention (the "hype") of an article in the research community at large, based on the underlying citation network.
BIP!Popularity provided by BIP!
influence
This indicator reflects the overall/total impact of an article in the research community at large, based on the underlying citation network (diachronically).
BIP!Influence provided by BIP!
impulse
This indicator reflects the initial momentum of an article directly after its publication, based on the underlying citation network.
BIP!Impulse provided by BIP!
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