Synthesis of gem-diamino derivatives on solid support |
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Authors: | Sonia CantelDamien Boeglin Marc RollandJean Martinez Jean-Alain Fehrentz |
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Institution: | Laboratoire des Aminoacides, Peptides et Protéines (LAPP), UMR 5810 CNRS Universités Montpellier I et II, Faculté de Pharmacie, 15 Avenue Charles Flahault, BP 14491, 34093 Montpellier Cédex 5, France |
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Abstract: | Anchoring of an α-amino-acid amide residue by its amine function to a carbamate resin followed by primary amide Hofmann rearrangement led to a gem-diamino residue linked to the resin. The generated primary amine could be acylated with various carboxylic compounds offering a large variety of molecules. Furthermore, this new solid-phase strategy allowed a reliable synthesis of a gem-diamino monomeric residue which could not be easily obtained in solution due to the limited stability of monocarbamate-protected gem-diaminoalkyl derivatives. |
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Keywords: | Hofmann rearrangement gem-diamino solid-phase synthesis |
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