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dc.contributor.authorReed, JH
dc.contributor.authorTurner, P
dc.contributor.authorKato, A
dc.contributor.authorHouston, TA
dc.contributor.authorSimone, MI
dc.date.accessioned2018-10-23T12:30:57Z
dc.date.available2018-10-23T12:30:57Z
dc.date.issued2013
dc.date.modified2014-06-11T03:11:33Z
dc.identifier.issn1600-5368
dc.identifier.doi10.1107/S1600536813015638
dc.identifier.urihttp://hdl.handle.net/10072/57516
dc.description.abstractIn the title compound (systematic name: {(3aS,5S,6R,6aS)-3a-[(benz­yloxy)meth­yl]-6-hy­droxy-2,2-di­methyl­tetra­hydro­furo[2,3-d][1,3]dioxol-5-yl}methyl 4-methyl­benzene­sulfonate), C23H28O8S, the absolute structure and relative stereochemistry of the four chiral centres have been established by X-ray crystallography, with the absolute configuration inferred from the use of L-sorbose as the starting material. The central furan­ose ring adopts a slightly twisted envelope conformation (with the C atom bearing the methyl­benzene­sulfonate substituent as the flap) from which three substituents depart pseudo-axially (-CH2-O-benzyl, -OH and one acetonide O atom) and two substituents pseudo-equatorially (-CH2-O-tosyl and second acetonide O atom). The dioxalane ring is in a flattened envelope conformation with the fused CH C atom as the flap. In the crystal, mol­ecules pack in columns along [010] linked by O-H...O hydrogen bonds involving the furan­ose hy­droxy group and furan­ose ether O atom.
dc.description.peerreviewedYes
dc.description.publicationstatusYes
dc.languageEnglish
dc.language.isoeng
dc.publisherWiley - Blackwell
dc.publisher.placeUnited States
dc.relation.ispartofstudentpublicationY
dc.relation.ispartofpagefromo1069
dc.relation.ispartofpagetoo1070
dc.relation.ispartofjournalActa Crystallographica. Section E Structure Reports Online
dc.relation.ispartofvolumeE69
dc.rights.retentionN
dc.subject.fieldofresearchChemical sciences
dc.subject.fieldofresearchOrganic chemical synthesis
dc.subject.fieldofresearchcode34
dc.subject.fieldofresearchcode340503
dc.title1-O-Benzyl-2,3-O-isopropylidene-6-O-tosyl-α-L-sorbofuranose
dc.typeJournal article
dc.type.descriptionC1 - Articles
dc.type.codeC - Journal Articles
dcterms.licensehttp://creativecommons.org/licenses/by/2.0/uk/legalcode
dc.description.versionVersion of Record (VoR)
gro.rights.copyright© The Author(s) 2013. For information about this journal please refer to the journal’s website. All articles published in Acta Crystallographica Section E are open access and distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. See http://creativecommons.org/licenses/by/2.0/uk/legalcode
gro.date.issued2013
gro.hasfulltextFull Text
gro.griffith.authorHouston, Todd A.


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