Stereoselective Synthesis of α- and β-Glycofuranosyl Amides by Traceless Ligation of Glycofuranosyl Azides
Articolo
Data di Pubblicazione:
2012
Citazione:
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]
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.
Tipologia IRIS:
01 - Articolo su periodico
Keywords:
azides; carbohydrates; glycomimetics; neo-glycoconjugates; Staudinger ligation; stereoselective synthesis
Elenco autori:
F. Nisic, G. Speciale, A. Bernardi
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