Synthesis and intramolecular nitrile oxide cycloaddition of 3,5'-ether-linked pseudooligosaccharide derivatives: an approach to chiral macrooxacycles.
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.
Sengupta
Jhimli
J
Indian Institute of Chemical Biology, 4, Raja S. C. Mullick Road, Kolkata 700032, India.
Mukhopadhyay
Ranjan
R
Bhattacharjya
Anup
A
Bhadbhade
Mohan M
MM
Bhosekar
Gaurav V
GV
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*
D007555:Isoxazoles; D047028:Macrocyclic Compounds; D009570:Nitriles; D009589:Nitrogen Oxides; D009844:Oligosaccharides