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., Peri, F., & Nicotra, F. (2004). Synthesis of Iminosugar Scaffolds for the Generation of Glycosidase inhibitor Libraries. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY(11), 2451-2470 [10.1002/ejoc.200300805].

Synthesis of Iminosugar Scaffolds for the Generation of Glycosidase inhibitor Libraries

LA FERLA, BARBARA;CIPOLLA, LAURA FRANCESCA;PERI, FRANCESCO;NICOTRA, FRANCESCO
2004

Abstract

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.
Articolo in rivista - Articolo scientifico
Scientifica
Carbohydrates; Glycosidase inhibitors; Imino sugars; Libraries; Scaffolds
English
LA FERLA, B., Bugada, P., Cipolla, L., Peri, F., & Nicotra, F. (2004). Synthesis of Iminosugar Scaffolds for the Generation of Glycosidase inhibitor Libraries. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY(11), 2451-2470 [10.1002/ejoc.200300805].
LA FERLA, B; Bugada, P; Cipolla, L; Peri, F; Nicotra, F
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/10281/14443
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