Ethyl 1-O-tert-butyldimethylsilyl-2,3-Oisopropylidene-5-[(20S)-tetrahydropyran2-yloxy]-D-glycero-a-D-manno-heptofuronate

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dc.contributor.affiliationUniversidade de Santiago de Compostela. Departamento de Química Inorgánicagl
dc.contributor.affiliationUniversidade de Santiago de Compostela. Departamento de Química Orgánicagl
dc.contributor.authorGonzález Soengas, Raquel María
dc.contributor.authorValencia Matarranz, Laura
dc.contributor.authorEstévez Cabanas, Juan Carlos
dc.contributor.authorEstévez Cabanas, Ramón José
dc.date.accessioned2020-07-15T11:10:21Z
dc.date.available2020-07-15T11:10:21Z
dc.date.issued2008
dc.description.abstractThe title compound {systematic name: (2S,3R)-ethyl 3- [(3aS,4R,6S,6aS)-6-tert-butyldimethylsilyloxy-2,2-dimethylperhydrofuro[3,4-d][1,3]dioxol-4-yl]-2-nitro-3-[(S)-tetrahydro-2H-pyran-2-yloxy]propanoate}, C23H41NO10Si, is the product of the Henry reaction of 1-O-tert-butyldimethylsilyl2,3-O-isopropylidene--d-lyxo-pentadialdo-1,4-furanose with ethyl nitroacetate and the subsequent protection of its C-5 hydroxy group as tetrahydropyranyl, in order to avoid the retro-Henry reaction. The tetrahydropyranyl group adopts a chair conformation. The absolute configuration, assumed from the synthesis, was confirmed from the diffraction datagl
dc.description.peerreviewedSIgl
dc.description.sponsorshipWe gratefully acknowledge the Spanish Education Secretary and the Xunta de Galicia for financial support and the Spanish Education Secretary for a grant to RGSgl
dc.identifier.citationSoengas, Raquel G. ; Valencia, Laura ; Estévez, Juan C. ; Estévez, Ramón J. (2008). Ethyl 1-O-tert-butyldimethylsilyl-2,3-O-isopropylidene-5-[(2′S)-tetrahydropyran-2-yloxy]-D-glycero-α-D-manno-heptofuronate. " Acta Crystallographica Section E", E64, o1478gl
dc.identifier.doi10.1107/S1600536808021193
dc.identifier.essn1600-5368
dc.identifier.issn2056-9890
dc.identifier.urihttp://hdl.handle.net/10347/23132
dc.language.isoenggl
dc.publisherInternational Union of Crystallographygl
dc.relation.publisherversionhttps://doi.org/10.1107/S1600536808021193gl
dc.rights© 2008 by the authors. Licensee International Union of Crystallography. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) licensegl
dc.rights.accessRightsopen accessgl
dc.rights.urihttp://creativecommons.org/licenses/by/4.0/
dc.subjectSingle-crystal X-ray studygl
dc.subjectR factor = 0.067gl
dc.subjectwR factor = 0.264gl
dc.subjectData-to-parameter ratio = 18.1.gl
dc.subjectMean (C–C) = 0.012 A˚gl
dc.subjectT = 293 Kgl
dc.titleEthyl 1-O-tert-butyldimethylsilyl-2,3-Oisopropylidene-5-[(20S)-tetrahydropyran2-yloxy]-D-glycero-a-D-manno-heptofuronategl
dc.typejournal articlegl
dc.type.hasVersionVoRgl
dspace.entity.typePublication
relation.isAuthorOfPublication86b5b898-6642-4dd7-b2ee-117e2f4838ff
relation.isAuthorOfPublication19cdf079-dc1b-48b2-8bc9-c73d3601f141
relation.isAuthorOfPublication.latestForDiscovery86b5b898-6642-4dd7-b2ee-117e2f4838ff

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