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Highly Stereoselective Synthesis of α-L-Olivomycosides via Trimethylsilyl Triflate Mediated Glycosidations of 1-<i>O</i>-Acetyl-4-<i>O</i>-isobutyryl-2,6-dideoxy-2-iodo-3-<i>C</i>-methyl-α-L-mannopyranose
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1993
Year
BiosynthesisBioorganic ChemistryTrimethylsilyl TriflateBiochemistryEngineeringNatural SciencesEnantioselective SynthesisGlycobiologyOrganic ChemistryStereoselective SynthesisChemistryNatural Product SynthesisSynthetic Chemistry2-Iodoolivomycarosyl-1α Acetate 4Biomolecular EngineeringGlycosylation
A highly stereoselective synthesis of α-L-olivomycosides via trimethylsilyl triflate mediated glycosidations of 2-iodoolivomycarosyl-1α acetate 4 is described. Evidence is presented that the intermediate iodonium ion 20 is configurationally stable under the reaction conditions.