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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
Synthesis and intramolecular nitrile oxide cycloaddition of 3,5'-ether-linked pseudooligosaccharide derivatives: an
Jhimli Sengupta1, Ranjan Mukhopadhyay, Anup Bhattacharjya
1Indian Institute of Chemical Biology, 4, Raja S. C. Mullick Road, Kolkata 700032, India.
Abstract:
3,5'-ether-linked pseudooligopentose derivatives were synthesized for the first time from readily available carbohydrate precursors. The 1,2-isopropylidene-protected ether-linked oligopentoses are potentially important as precursors of novel RNA analogues. Intramolecular cycloaddition of the nitrile oxides prepared from these derivatives led to the diastereoselective formation of chiral isoxazolines fused to 10-16-membered oxacycles. The stereochemistry of some of these isoxazolines was established by X-ray diffraction and NOESY analysis.
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