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Iodonium Ion Promoted Cyclization: A Convenient Approach to Glycosyl Donors of 3-Deoxy-D-<i>manno</i>-2-octulosonic Acid (KDO)
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1990
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Glycosyl DonorsNovel OrganocatalystsBioorganic ChemistryEngineeringBiochemistryConvenient ApproachNatural SciencesDiversity-oriented SynthesisIodonium Sym-dicollidine PerchlorateOrganic ChemistryOrganometallic Catalysis3-Deoxy-d-manno-2-octulosonic AcidStereoselective SynthesisChemistryNatural Product SynthesisSynthetic ChemistryEnantioselective SynthesisBiomolecular Engineering
Cyclization of methyl 3-deoxy-4,5:7,8-di-O-isopropylidene-D-manno-octulonate diethyl dithioacetal with iodonium sym-dicollidine perchlorate or N-iodosuccinimide yields methyl 2,3-dideoxy-4,5:7,8-di-O-isopropylidene-D-manno-oct-2-enulosonate (KDO-glycal) or the ethyl 2-thio-α-glycoside of 3-deoxy-D-manno-2-octulosonic acid, respectively. The latter compounds can be employed as glycosyl donors of 3-deoxy-D-manno-2-octulosonic acid.