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Synthesis of 3'-C-Substituted-2',3'-Dideoxynucleosldes as Potential Antcaids Agents
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1989
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Free Radical MethodologyBioorganic ChemistryEngineeringNatural SciencesNmr Noe ExperimentsOrganic ChemistryStereo-chemical AssignmentStereoselective SynthesisChemistryHeterocycle ChemistryNatural Product SynthesisSynthetic ChemistryPotential Antcaids AgentsBiomolecular Engineering
Abstract In this paper we report an efficient synthetic route to some novel 3′-C-substituted-2,3′-dideoxy-nucleosides. The critical 3′- C-C bond was constructed by an application of free radical methodology. This type of reaction was found to be stereoselective forming exclusively the 3′-“down” isomer. The stereo-chemical assignment at C-3′ was confirmed by both nmr nOe experiments and single crystal X-ray analysis.