Short synthesis, X-ray and conformational analysis of a cyclic peracetylated L-sorbose-derived nitrone, a useful intermediate towards N–O-containing D-gluco-iminosugars - Archive ouverte HAL Accéder directement au contenu
Article Dans Une Revue New Journal of Chemistry Année : 2018

Short synthesis, X-ray and conformational analysis of a cyclic peracetylated L-sorbose-derived nitrone, a useful intermediate towards N–O-containing D-gluco-iminosugars

Résumé

The synthesis of the peracetylated ketonitrone 4 is described in four steps from L-sorbose. This cyclic nitrone is crystalline and proved to preferentially adopt a 4H3 conformation with all acetate groups in pseudo-axial orientation. Nitrone 4 undergoes regioselective cycloadditions with alkynes, affording tetra-O-acetyl-isoxazolines with good yields and stereoselectivities (4 : 1 to 9 : 1 diastereomeric ratio). Nitrone 4 and the obtained isoxazolines were smoothly deacetylated to produce the polyhydroxylated nitrone 5 and novel iminosugars containing an isoxazoline motif. Evaluation of their glycosidase inhibitory activity demonstrated their rather weak, but selective affinity for a variety of enzymes.
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hal-02048186 , version 1 (25-02-2019)

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Salia Tangara, Alice Kanazawa, Martine Fayolle, Christian Philouze, Jean-François Poisson, et al.. Short synthesis, X-ray and conformational analysis of a cyclic peracetylated L-sorbose-derived nitrone, a useful intermediate towards N–O-containing D-gluco-iminosugars. New Journal of Chemistry, 2018, 42 (20), pp.16735-16743. ⟨10.1039/C8NJ03868F⟩. ⟨hal-02048186⟩
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