title: Synthesis and intramolecular nitrile oxide cycloaddition of 3,5'-ether-linked pseudooligosaccharide derivatives: an approach to chiral macrooxacycles.
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.
authors.affiliation: Indian Institute of Chemical Biology, 4, Raja S. C. Mullick Road, Kolkata 700032, India.
authors.forename: Jhimli
authors.initials: J
authors.lastname: Sengupta
authors.forename: Ranjan
authors.initials: R
authors.lastname: Mukhopadhyay
authors.forename: Anup
authors.initials: A
authors.lastname: Bhattacharjya
authors.forename: Mohan M
authors.initials: MM
authors.lastname: Bhadbhade
authors.forename: Gaurav V
authors.initials: GV
authors.lastname: Bhosekar
mesh_terms: D003500:Cyclization; D007555:Isoxazoles / Q000737:chemistry*; D047028:Macrocyclic Compounds / Q000138:chemical synthesis*; D015394:Molecular Structure; D009570:Nitriles / Q000737:chemistry*; D009589:Nitrogen Oxides / Q000737:chemistry*; D009844:Oligosaccharides / Q000138:chemical synthesis* / Q000737:chemistry*
chemical_list: D007555:Isoxazoles; D047028:Macrocyclic Compounds; D009570:Nitriles; D009589:Nitrogen Oxides; D009844:Oligosaccharides