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Article Dans Une Revue SYNLETT Année : 2009

Expeditious stereoselective synthesis of L-iminosugars precursors via a Mitsunobu reaction

Résumé

An efficient stereoselective synthesis of l-imino-C-gulosides is disclosed. Starting from the 2,3:4,6-di-O-isopropylidene-d-mannopyranose the synthetic pathway involves first a Wittig reaction with CMPP to introduce the carbon at the pseudo-anomeric position, followed by a Michael reaction under ultrasound activation to introduce the nitrogen center, and finally a Mitsunobu reaction for the ring closure leading to the C-iminosugar from the l-series

Domaines

Chimie organique
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Dates et versions

hal-00582930 , version 1 (04-04-2011)

Identifiants

Citer

Antoine Bussière, Véronique Barragan-Montero, Khalid Null Oumzil, Jean-Yves Winum, Jean-Louis Montero. Expeditious stereoselective synthesis of L-iminosugars precursors via a Mitsunobu reaction. SYNLETT, 2009, 6, pp.978-980. ⟨10.1055/s-0028-1088209⟩. ⟨hal-00582930⟩
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