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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.
- Source :
-
New Journal of Chemistry . 10/21/2018, Vol. 42 Issue 20, p16735-16743. 9p. - Publication Year :
- 2018
-
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. [ABSTRACT FROM AUTHOR]
- Subjects :
- *MOLECULAR conformation
*IMINOSUGARS
*CHEMICAL synthesis
Subjects
Details
- Language :
- English
- ISSN :
- 11440546
- Volume :
- 42
- Issue :
- 20
- Database :
- Academic Search Index
- Journal :
- New Journal of Chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 132211049
- Full Text :
- https://doi.org/10.1039/c8nj03868f