About: Synthesis of All Configurational Isomers of 1,6-Anhydro-2,3,4-trideoxy-2,3-epimino-4-fluoro-β-D-hexopyranoses

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About: Synthesis of All Configurational Isomers of 1,6-Anhydro-2,3,4-trideoxy-2,3-epimino-4-fluoro-β-D-hexopyranoses Goto Sponge NotDistinct Permalink

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rdf:type	skos:Concept http://linked.opendata.cz/ontology/domain/vavai/Vysledek
Description	Fluorinated hexopyranoses are important synthetic targets because of their utilization as probes in enzymology, medicine and structure - reactivity studies. We have prepared a full series of 1,6-anhydro-2,3,4-deoxy-4-fluoro-2,3-epimino-β-D-hexopyranoses. The key step was reaction of trans-2,3-azidosulfonates possessing a free C-4 hydroxyl with DAST and subsequent LiAlH4 reduction. Nucleophilic displacement of the hydroxyl activated by DAST proceeded without rearrangement and with moderate to good yields. A convenient synthesis of D-manno epimine from a readily available 3-benzylamino derivative was also developed. Fluorinated hexopyranoses are important synthetic targets because of their utilization as probes in enzymology, medicine and structure - reactivity studies. We have prepared a full series of 1,6-anhydro-2,3,4-deoxy-4-fluoro-2,3-epimino-β-D-hexopyranoses. The key step was reaction of trans-2,3-azidosulfonates possessing a free C-4 hydroxyl with DAST and subsequent LiAlH4 reduction. Nucleophilic displacement of the hydroxyl activated by DAST proceeded without rearrangement and with moderate to good yields. A convenient synthesis of D-manno epimine from a readily available 3-benzylamino derivative was also developed. (en)
Title	Synthesis of All Configurational Isomers of 1,6-Anhydro-2,3,4-trideoxy-2,3-epimino-4-fluoro-β-D-hexopyranoses Synthesis of All Configurational Isomers of 1,6-Anhydro-2,3,4-trideoxy-2,3-epimino-4-fluoro-β-D-hexopyranoses (en)
skos:prefLabel	Synthesis of All Configurational Isomers of 1,6-Anhydro-2,3,4-trideoxy-2,3-epimino-4-fluoro-β-D-hexopyranoses Synthesis of All Configurational Isomers of 1,6-Anhydro-2,3,4-trideoxy-2,3-epimino-4-fluoro-β-D-hexopyranoses (en)
skos:notation	RIV/67985858:_____/10:00343244!RIV11-AV0-67985858
http://linked.open...avai/riv/aktivita	P Z
http://linked.open...avai/riv/aktivity	P(IAA400720703), P(IAA400720706), Z(AV0Z40550506), Z(AV0Z40720504), Z(MSM0021620857), Z(MSM0021627501)
http://linked.open...iv/cisloPeriodika	10
http://linked.open...vai/riv/dodaniDat	2011
http://linked.open...aciTvurceVysledku	Sýkora, Jan Karban, Jindřich
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	Ústav chemických procesů AV ČR, v. v. i.
http://linked.open...dnocenehoVysledku	291512
http://linked.open...ai/riv/idVysledku	RIV/67985858:_____/10:00343244
http://linked.open...riv/jazykVysledku	eng - angličtina
http://linked.open.../riv/klicovaSlova	fluorinated hexopyranoses; synthesis; experiments (en)
http://linked.open.../riv/klicoveSlovo	fluorinated hexopyranoses experiments synthesis
http://linked.open...odStatuVydavatele	US - Spojené státy americké
http://linked.open...ontrolniKodProRIV	[25A1F6213EFE]
http://linked.open...i/riv/nazevZdroje	Journal of Organic Chemistry
http://linked.open...in/vavai/riv/obor	CF
http://linked.open...ichTvurcuVysledku	2 (xsd:int)
http://linked.open...cetTvurcuVysledku	6 (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 Reactivity of asymmetrically substituted epimino pyranoses
http://linked.open...UplatneniVysledku	2010
http://linked.open...v/svazekPeriodika	75
http://linked.open...iv/tvurceVysledku	Buděšínský, Miloš Císařová, I. Padělková, Z. Sýkora, Jan Karban, Jindřich Kroutil, J.
http://linked.open...ain/vavai/riv/wos	000277531200033
http://linked.open...n/vavai/riv/zamer	Regulace biologických procesů: Chemické modulátory vybraných systémů významných pro medicínu a zemědělství 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 Aimed preparation of special compounds and materials and investigation of their physical and chemical properties and supramolecular structures
issn	0022-3263
number of pages	4 (xsd:int)
is http://linked.open...avai/riv/vysledek of	Synthesis of All Configurational Isomers of 1,6-Anhydro-2,3,4-trideoxy-2,3-epimino-4-fluoro-β-D-hexopyranoses Synthesis of All Configurational Isomers of 1,6-Anhydro-2,3,4-trideoxy-2,3-epimino-4-fluoro-β-D-hexopyranoses Synthesis of All Configurational Isomers of 1,6-Anhydro-2,3,4-trideoxy-2,3-epimino-4-fluoro-β-D-hexopyranoses

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