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Article Dans Une Revue Organic Letters Année : 2022

Stereoselective Access to Iminosugar C, C-Glycosides from 6-Azidoketopyranoses

Résumé

We report the synthesis of iminosugar C,C-glycosides starting from 6-azidoketopyranoses. Their Staudinger-azaWittig-mediated cyclization provided bicyclic N,O-acetals, which were stereoselectively opened with AllMgBr to afford β-hydroxyazepanes with a quaternary carbon α to the nitrogen. Their ring contraction via a β-aminoalcohol rearrangement produced the six-membered l-iminosugars with two functional handles at the pseudoanomeric position. Inversion of the free OH at the azepane level furnished the d-iminosugars.
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hal-03775104 , version 1 (17-04-2024)

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Zakaria Debbah, Jérôme C. Marrot, Nicolas Auberger, Jérôme Désiré, Yves Blériot. Stereoselective Access to Iminosugar C, C-Glycosides from 6-Azidoketopyranoses. Organic Letters, 2022, 24 (25), pp.4542-4546. ⟨10.1021/acs.orglett.2c01560⟩. ⟨hal-03775104⟩
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