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2-Nitro-thioglycosides : α- and β-Selective Generation and Their Potential as β-Selective Glycosyl Donors

2-Nitro-thioglycosides : α- and β-Selective Generation and Their Potential as β-Selective Glycosyl Donors

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PENG, Peng, Yiqun GENG, Inigo GÖTTKER-SCHNETMANN, Richard R. SCHMIDT, 2015. 2-Nitro-thioglycosides : α- and β-Selective Generation and Their Potential as β-Selective Glycosyl Donors. In: Organic Letters. 17(6), pp. 1421-1424. ISSN 1523-7060. eISSN 1523-7052

@article{Peng20152-Nit-31382, title={2-Nitro-thioglycosides : α- and β-Selective Generation and Their Potential as β-Selective Glycosyl Donors}, year={2015}, doi={10.1021/acs.orglett.5b00295}, number={6}, volume={17}, issn={1523-7060}, journal={Organic Letters}, pages={1421--1424}, author={Peng, Peng and Geng, Yiqun and Göttker-Schnetmann, Inigo and Schmidt, Richard R.} }

<rdf:RDF xmlns:rdf="http://www.w3.org/1999/02/22-rdf-syntax-ns#" xmlns:bibo="http://purl.org/ontology/bibo/" xmlns:dc="http://purl.org/dc/elements/1.1/" xmlns:dcterms="http://purl.org/dc/terms/" xmlns:xsd="http://www.w3.org/2001/XMLSchema#" > <rdf:Description rdf:about="https://kops.uni-konstanz.de/rdf/resource/123456789/31382"> <dc:contributor>Schmidt, Richard R.</dc:contributor> <dc:language>eng</dc:language> <dc:date rdf:datatype="http://www.w3.org/2001/XMLSchema#dateTime">2015-07-08T06:13:58Z</dc:date> <dc:contributor>Geng, Yiqun</dc:contributor> <dcterms:available rdf:datatype="http://www.w3.org/2001/XMLSchema#dateTime">2015-07-08T06:13:58Z</dcterms:available> <dc:creator>Göttker-Schnetmann, Inigo</dc:creator> <dcterms:abstract xml:lang="eng">Michael-type addition of thiolates to 2-nitro-d-glucal or to 2-nitro-d-galactal derivatives readily provides 2-deoxy-2-nitro-1-thioglycosides. Kinetic and thermodynamic reaction control permitted formation of either the α- or preferentially the β-anomers, respectively. Addition of achiral and chiral thiourea derivatives to the reaction mixture increased the reaction rate; the outcome is substrate-controlled. The 2-deoxy-2-nitro-1-thioglycosides are excellent glycosyl donors under arylsulfenyl chloride/silver triflate (ArSCl/AgOTf) activation, and they provide, anchimerically assisted by the nitro group, mostly β-glycosides.</dcterms:abstract> <dcterms:title>2-Nitro-thioglycosides : α- and β-Selective Generation and Their Potential as β-Selective Glycosyl Donors</dcterms:title> <dc:creator>Schmidt, Richard R.</dc:creator> <dc:creator>Peng, Peng</dc:creator> <dc:contributor>Peng, Peng</dc:contributor> <dcterms:issued>2015</dcterms:issued> <dc:creator>Geng, Yiqun</dc:creator> <dc:contributor>Göttker-Schnetmann, Inigo</dc:contributor> <bibo:uri rdf:resource="http://kops.uni-konstanz.de/handle/123456789/31382"/> </rdf:Description> </rdf:RDF>

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