A highly stereoselective synthesis of a- or b-glycofuranosyl amides based on the traceless Staudinger ligation of glycofuranosyl azides of the galacto, ribo, and arabino series with 2-diphenylphosphanyl- phenyl esters has been developed. Both a- and b-isomers can be obtained with excellent selectivity from a common, easily available precursor. The process does not depend on the anomeric configuration of the starting azide but appears to be controlled by the C2 configuration and by the protection/deprotection state of the substrates. A mechanistic interpretation of the results, supported by 31P NMR experiments, is offered and merged with our previous mechanistic analysis of pyranosyl azide ligation reactions.

Stereoselective Synthesis of α- and β-Glycofuranosyl Amides by Traceless Ligation of Glycofuranosyl Azides / F. Nisic, G. Speciale, A. Bernardi. - In: CHEMISTRY-A EUROPEAN JOURNAL. - ISSN 0947-6539. - 18:22(2012), pp. 6895-6906. [10.1002/chem.201200309]

Stereoselective Synthesis of α- and β-Glycofuranosyl Amides by Traceless Ligation of Glycofuranosyl Azides

F. Nisic
Primo
;
A. Bernardi
Ultimo
2012

Abstract

A highly stereoselective synthesis of a- or b-glycofuranosyl amides based on the traceless Staudinger ligation of glycofuranosyl azides of the galacto, ribo, and arabino series with 2-diphenylphosphanyl- phenyl esters has been developed. Both a- and b-isomers can be obtained with excellent selectivity from a common, easily available precursor. The process does not depend on the anomeric configuration of the starting azide but appears to be controlled by the C2 configuration and by the protection/deprotection state of the substrates. A mechanistic interpretation of the results, supported by 31P NMR experiments, is offered and merged with our previous mechanistic analysis of pyranosyl azide ligation reactions.
azides; carbohydrates; glycomimetics; neo-glycoconjugates; Staudinger ligation; stereoselective synthesis
Settore CHIM/06 - Chimica Organica
2012
Article (author)
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2434/191709
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