About: Skeletal Rearrangements Resulting from Reactions of 1,6:2,3- and 1,6:3,4-Dianhydro-beta-D-hexopyranoses with Diethylaminosulphur Trifluoride

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About: Skeletal Rearrangements Resulting from Reactions of 1,6:2,3- and 1,6:3,4-Dianhydro-beta-D-hexopyranoses with Diethylaminosulphur Trifluoride Goto Sponge NotDistinct Permalink

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rdf:type	skos:Concept http://linked.opendata.cz/ontology/domain/vavai/Vysledek
rdfs:seeAlso	http://dx.doi.org/10.1039/c1ob06336g
Description	A complete series of eight 1,6:2,3- and 1,6:3,4-dianhydro-beta-D-hexopyranoses were subjected to fluorination with DAST. The 1,6:3,4-dianhydropyranoses yielded solely products of skeletal rearrangement resulting from migration of the tetrahydropyran oxygen (educts of D-altro and D-talo configuration) or of the 1,6-anhydro bridge oxygen (D-allo, D-galacto). The major products yielded by the 1,6:2,3-dianhydropyranoses were compounds arising from nucleophilic substitution, with configuration at C4 either retained (D-talo, D-gulo) or inverted (D-manno), or from C6 migration (D-allo). The minor products in the 1,6:2,3-series resulted from migration of the tetrahydropyran oxygen (D-gulo) or the oxirane oxygen (D-manno), or from nucleophilic substitution with retention of configuration (D-manno). The structure of most of the rearranged products was verified by X-ray crystallography. A complete series of eight 1,6:2,3- and 1,6:3,4-dianhydro-beta-D-hexopyranoses were subjected to fluorination with DAST. The 1,6:3,4-dianhydropyranoses yielded solely products of skeletal rearrangement resulting from migration of the tetrahydropyran oxygen (educts of D-altro and D-talo configuration) or of the 1,6-anhydro bridge oxygen (D-allo, D-galacto). The major products yielded by the 1,6:2,3-dianhydropyranoses were compounds arising from nucleophilic substitution, with configuration at C4 either retained (D-talo, D-gulo) or inverted (D-manno), or from C6 migration (D-allo). The minor products in the 1,6:2,3-series resulted from migration of the tetrahydropyran oxygen (D-gulo) or the oxirane oxygen (D-manno), or from nucleophilic substitution with retention of configuration (D-manno). The structure of most of the rearranged products was verified by X-ray crystallography. (en)
Title	Skeletal Rearrangements Resulting from Reactions of 1,6:2,3- and 1,6:3,4-Dianhydro-beta-D-hexopyranoses with Diethylaminosulphur Trifluoride Skeletal Rearrangements Resulting from Reactions of 1,6:2,3- and 1,6:3,4-Dianhydro-beta-D-hexopyranoses with Diethylaminosulphur Trifluoride (en)
skos:prefLabel	Skeletal Rearrangements Resulting from Reactions of 1,6:2,3- and 1,6:3,4-Dianhydro-beta-D-hexopyranoses with Diethylaminosulphur Trifluoride Skeletal Rearrangements Resulting from Reactions of 1,6:2,3- and 1,6:3,4-Dianhydro-beta-D-hexopyranoses with Diethylaminosulphur Trifluoride (en)
skos:notation	RIV/00216208:11310/12:10127585!RIV13-MSM-11310___
http://linked.open...avai/riv/aktivita	I P Z
http://linked.open...avai/riv/aktivity	I, P(IAA400720706), Z(AV0Z40720504), Z(MSM0021620857)
http://linked.open...iv/cisloPeriodika	2
http://linked.open...vai/riv/dodaniDat	2013
http://linked.open...aciTvurceVysledku	Císařová, Ivana
http://linked.open.../riv/druhVysledku	J - Článek v odborném periodiku
http://linked.open...iv/duvernostUdaju	S - Úplné a pravdivé údaje nepodléhající ochraně podle zvláštních právních předpisů
http://linked.open...titaPredkladatele	Univerzita Karlova v Praze / Přírodovědecká fakulta
http://linked.open...dnocenehoVysledku	168230
http://linked.open...ai/riv/idVysledku	RIV/00216208:11310/12:10127585
http://linked.open...riv/jazykVysledku	eng - angličtina
http://linked.open.../riv/klicovaSlova	benzyloxy group; X-ray crystallography; carbohydrates (en)
http://linked.open.../riv/klicoveSlovo	X-ray crystallography carbohydrates benzyloxy group
http://linked.open...odStatuVydavatele	GB - Spojené království Velké Británie a Severního Irska
http://linked.open...ontrolniKodProRIV	[062ED49C4F68]
http://linked.open...i/riv/nazevZdroje	Organic and Biomolecular Chemistry
http://linked.open...in/vavai/riv/obor	CF
http://linked.open...ichTvurcuVysledku	1 (xsd:int)
http://linked.open...cetTvurcuVysledku	5 (xsd:int)
http://linked.open...vavai/riv/projekt	Structure of silyl moieties through J(29Si-13C) couplings as determined by triple {1H, 13C}29Si NMR experiments
http://linked.open...UplatneniVysledku	2012
http://linked.open...v/svazekPeriodika	10
http://linked.open...iv/tvurceVysledku	Císařová, Ivana Sýkora, Jan Karban, Jindřich Strašák, Tomáš Červenková Šťastná, Lucie
http://linked.open...ain/vavai/riv/wos	000298555700028
http://linked.open...n/vavai/riv/zamer	Investigation of multiphase reacting systems for the design of processes important in synthesis and preparation of novel materials, in energy production and in environmental protection Nové molekulární systémy pro pokročilé aplikace prospěšné pro zdraví a šetrné k životnímu prostředí
issn	1477-0520
number of pages	10 (xsd:int)
http://bibframe.org/vocab/doi	10.1039/c1ob06336g
http://localhost/t...ganizacniJednotka	11310

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