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.
|Titolo:||Stereoselective Synthesis of α- and β-Glycofuranosyl Amides by Traceless Ligation of Glycofuranosyl Azides|
NISIC, FILIPPO (Primo)
BERNARDI, ANNA (Ultimo)
|Parole Chiave:||azides; carbohydrates; glycomimetics; neo-glycoconjugates; Staudinger ligation; stereoselective synthesis|
|Settore Scientifico Disciplinare:||Settore CHIM/06 - Chimica Organica|
|Data di pubblicazione:||2012|
|Digital Object Identifier (DOI):||http://dx.doi.org/10.1002/chem.201200309|
|Appare nelle tipologie:||01 - Articolo su periodico|