dc.contributor.author | Reed, JH | |
dc.contributor.author | Turner, P | |
dc.contributor.author | Kato, A | |
dc.contributor.author | Houston, TA | |
dc.contributor.author | Simone, MI | |
dc.date.accessioned | 2018-10-23T12:30:57Z | |
dc.date.available | 2018-10-23T12:30:57Z | |
dc.date.issued | 2013 | |
dc.date.modified | 2014-06-11T03:11:33Z | |
dc.identifier.issn | 1600-5368 | |
dc.identifier.doi | 10.1107/S1600536813015638 | |
dc.identifier.uri | http://hdl.handle.net/10072/57516 | |
dc.description.abstract | In 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.peerreviewed | Yes | |
dc.description.publicationstatus | Yes | |
dc.language | English | |
dc.language.iso | eng | |
dc.publisher | Wiley - Blackwell | |
dc.publisher.place | United States | |
dc.relation.ispartofstudentpublication | Y | |
dc.relation.ispartofpagefrom | o1069 | |
dc.relation.ispartofpageto | o1070 | |
dc.relation.ispartofjournal | Acta Crystallographica. Section E Structure Reports Online | |
dc.relation.ispartofvolume | E69 | |
dc.rights.retention | N | |
dc.subject.fieldofresearch | Chemical sciences | |
dc.subject.fieldofresearch | Organic chemical synthesis | |
dc.subject.fieldofresearchcode | 34 | |
dc.subject.fieldofresearchcode | 340503 | |
dc.title | 1-O-Benzyl-2,3-O-isopropylidene-6-O-tosyl-α-L-sorbofuranose | |
dc.type | Journal article | |
dc.type.description | C1 - Articles | |
dc.type.code | C - Journal Articles | |
dcterms.license | http://creativecommons.org/licenses/by/2.0/uk/legalcode | |
dc.description.version | Version 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.issued | 2013 | |
gro.hasfulltext | Full Text | |
gro.griffith.author | Houston, Todd A. | |