We have synthesized imino sugar scaffolds bearing two points of diversity - the stereocenters located in α positions relative to the nitrogen atom - and three points of orthogonal derivatization - a carboxylic function, the primary hydroxy group, and the ring nitrogen atom. The key steps in the synthetic approach are the chain elongation of aldehyde 5 with the formation of an α,β-unsaturated ester, the Michael addition of an amine, and the final cyclization. This strategy leads to the preparation of different N-substituted imino sugar analogues having both α and β structures and of both D and L stereochemistry. Different derivatives have been prepared from the scaffolds we obtained. The carboxymethyl group was coupled to the amino function of different amino acids to afford compounds 30-34, while the selectively accessible primary hydroxy group has been substituted with an azido group to afford compounds 24-26. © Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.
La Ferla, B., Bugada, P., Cipolla, L.F., Peri, F., & Nicotra, F. (2004). Synthesis of Iminosugar Scaffolds for the Generation of Glycosidase inhibitor Libraries. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY(11), 2451-2470.
Citazione: | La Ferla, B., Bugada, P., Cipolla, L.F., Peri, F., & Nicotra, F. (2004). Synthesis of Iminosugar Scaffolds for the Generation of Glycosidase inhibitor Libraries. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY(11), 2451-2470. |
Tipo: | Articolo in rivista - Articolo scientifico |
Carattere della pubblicazione: | Scientifica |
Presenza di un coautore afferente ad Istituzioni straniere: | No |
Titolo: | Synthesis of Iminosugar Scaffolds for the Generation of Glycosidase inhibitor Libraries |
Autori: | La Ferla, B; Bugada, P; Cipolla, LF; Peri, F; Nicotra, F |
Autori: | |
Data di pubblicazione: | 2004 |
Lingua: | English |
Rivista: | EUROPEAN JOURNAL OF ORGANIC CHEMISTRY |
Digital Object Identifier (DOI): | http://dx.doi.org/10.1002/ejoc.200300805 |
Appare nelle tipologie: | 01 - Articolo su rivista |