Synthesis of 2-(1-aminocyclopropyl)pyrrolidine-3,4-diol derivatives applying titanium-mediated reaction conditions - Le Mans Université Accéder directement au contenu
Article Dans Une Revue Tetrahedron Année : 2012

Synthesis of 2-(1-aminocyclopropyl)pyrrolidine-3,4-diol derivatives applying titanium-mediated reaction conditions

Résumé

The titanium-mediated cyclopropanation reaction using Ti(OiPr)3Me/EtMgBr/BF3·OEt2 has been applied to various 2-cyanopyrrolidines for the synthesis of functionalized 2-(1-aminocyclopropyl)pyrrolidine-3,4-diol derivatives (dideoxyiminoalditols). Under the same experimental conditions the trans-5-azidomethyl-2-cyanopyrrolidine derivative was not cyclopropanated but reduced into the corresponding 5-amino-2-cyano derivative. After polyol deprotection 2-(1-aminocyclopropyl)pyrrolidine-3,4-diols were obtained and their inhibitory activity towards 13 glycosidases has been evaluated. (2S,3S,4R,5S)-2-(1-Aminocyclopropyl)-5-methylpyrrolidine-3,4-diol (38), which has the same absolute configuration as l-fucose, is a moderate (IC50=44 μM), but selective, inhibitor of α-l-fucosidase from human placenta.

Dates et versions

hal-00711775 , version 1 (25-06-2012)

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Delphine Declerck, Albert Nguyen van Nhien, Solen Josse, Jan Szymoniak, Philippe Bertus, et al.. Synthesis of 2-(1-aminocyclopropyl)pyrrolidine-3,4-diol derivatives applying titanium-mediated reaction conditions. Tetrahedron, 2012, 68 (6), pp.1802-1809. ⟨10.1016/j.tet.2011.12.024⟩. ⟨hal-00711775⟩
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