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Issue 20, 2018
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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

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Abstract

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.

Graphical abstract: 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

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Publication details

The article was received on 01 Aug 2018, accepted on 06 Sep 2018 and first published on 18 Sep 2018


Article type: Paper
DOI: 10.1039/C8NJ03868F
Citation: New J. Chem., 2018,42, 16735-16743
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    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

    S. Tangara, A. Kanazawa, M. Fayolle, C. Philouze, J. Poisson, J. Behr and S. Py, New J. Chem., 2018, 42, 16735
    DOI: 10.1039/C8NJ03868F

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