Synthesis of 2-(1-aminocyclopropyl)pyrrolidine-3,4-diol derivatives applying titanium-mediated reaction conditions |
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| Authors: | Delphine Declerck Albert Nguyen Van Nhien Solen Josse Jan Szymoniak Philippe Bertus Claudia Bello Pierre Vogel Denis Postel |
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| Affiliation: | 1. Laboratoire des glucides UMR6219, Université de Picardie Jules Verne, Faculté des Sciences, 33 rue Saint-Leu, 80039 Amiens, France;2. Université de Reims Champagne-Ardenne, UMR-CNRS 6229, Institut de Chimie Moléculaire de Reims, BP 1039, 51687 Reims Cedex 02, France;3. Université du Maine, UMR-CNRS 6011, Unité de Chimie Organique Moléculaire et Macromoléculaire, Avenue Olivier Messiaen, 72085 Le Mans Cedex 9, France;4. Laboratoire de glycochimie et de synthèse asymétrique (LGSA), Ecole Polytechnique Fédérale de Lausanne (EPFL), Batochime, CH 1015 Lausanne, Switzerland |
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| Abstract: | ![]()
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. |
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