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.
Titolo: | A Simple Synthetic Access to Differently 4-Substituted Neu5Ac2en Glycals Combining Elements of Molecules with Anti-Neuraminidase Activity |
Autori: | ALLEVI, PIETRO (Primo) ROTA, PAOLA (Secondo) GREGORIO, ANTONIO (Penultimo) ANASTASIA, MARIO (Ultimo) |
Parole Chiave: | Carbohydrates; Glycals; Nucleophilic substitution; Rearrangement; Sialic acids |
Settore Scientifico Disciplinare: | Settore BIO/10 - Biochimica |
Data di pubblicazione: | 2013 |
Rivista: | |
Tipologia: | Article (author) |
Digital Object Identifier (DOI): | http://dx.doi.org/10.1002/ejoc.201300154 |
Appare nelle tipologie: | 01 - Articolo su periodico |