A protocol for direct access to C-4-functionalized Neu5Ac2en derivatives by allylic substitution of an α-acetoxy group with various nucleophiles is reported. The DANA acetamido group is exchanged for a trifluoroacetylamido group (as in FANA) to avoid the formation of a stable 4,5-oxazoline. With thiols, the reaction involves an initial attack at the anomeric carbon (Ferrier reaction) under kinetic control, followed by an equilibration of the nucleophile to the thermodynamically more stable 4-position.
A Simple Synthetic Access to Differently 4-Substituted Neu5Ac2en Glycals Combining Elements of Molecules with Anti-Neuraminidase Activity / P. Allevi, P. Rota, I.S. Agnolin, A. Gregorio, M. Anastasia. - In: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. - ISSN 1434-193X. - 2013:19(2013), pp. 4065-4077. [10.1002/ejoc.201300154]
A Simple Synthetic Access to Differently 4-Substituted Neu5Ac2en Glycals Combining Elements of Molecules with Anti-Neuraminidase Activity
P. AlleviPrimo
;P. RotaSecondo
;I.S. Agnolin;A. GregorioPenultimo
;M. AnastasiaUltimo
2013
Abstract
A protocol for direct access to C-4-functionalized Neu5Ac2en derivatives by allylic substitution of an α-acetoxy group with various nucleophiles is reported. The DANA acetamido group is exchanged for a trifluoroacetylamido group (as in FANA) to avoid the formation of a stable 4,5-oxazoline. With thiols, the reaction involves an initial attack at the anomeric carbon (Ferrier reaction) under kinetic control, followed by an equilibration of the nucleophile to the thermodynamically more stable 4-position.Pubblicazioni consigliate
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