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Synthesis and Intramolecular Nitrile Oxide Cycloaddition of 3,5‘-Ether-Linked Pseudooligosaccharide Derivatives: An Approach to Chiral Macrooxacycles
journal contribution
posted on 2005-10-14, 00:00 authored by Jhimli Sengupta, Ranjan Mukhopadhyay, Anup Bhattacharjya, Mohan M. Bhadbhade, Gaurav V. Bhosekar3,5‘-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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Intramolecular cycloadditionIntramolecular Nitrile Oxide CycloadditionDerivativeApproachNOESY analysisoxacyclederivativecarbohydrate precursorsSynthesiPseudooligosaccharideChiraloligopentosediastereoselective formationchiral isoxazolinesstereochemistrynitrile oxidesnovel RNA analoguesdiffractionMacrooxacyclememberedpseudooligopentose
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