Açık Akademik Arşiv Sistemi

Stereospecific synthesis of a DL-gala-aminoquercitol derivative

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dc.contributor.authors Kurbanoglu, NI; Celik, M; Kilic, H; Alp, C; Sahin, E; Balci, M;
dc.date.accessioned 2020-02-24T13:29:09Z
dc.date.available 2020-02-24T13:29:09Z
dc.date.issued 2010
dc.identifier.citation Kurbanoglu, NI; Celik, M; Kilic, H; Alp, C; Sahin, E; Balci, M; (2010). Stereospecific synthesis of a DL-gala-aminoquercitol derivative. TETRAHEDRON, 66, 3489-3485
dc.identifier.issn 0040-4020
dc.identifier.uri https://doi.org/10.1016/j.tet.2010.03.028
dc.identifier.uri https://hdl.handle.net/20.500.12619/44218
dc.description.abstract A new aminoquercitol derivative was synthesized starting from 1,4-cyclohexadiene. Photooxygenation of cyclohexa-1,4-diene afforded anti-2,3-dioxabicyclo[2.2.2]oct-7-en-5-yl hydroperoxicle as the main product. The formed hydroperoxy endoperoxide was reduced with LiAlH(4) to produce anti-2,3-dioxabicyclo[2.2.2]oct-7-en-5-ol. Protection of alcohol with acetyl chloride followed by reduction of the endoperoxide with thiourea, and then palladium-catalyzed ionization/cyclization reaction gave an oxazolidinone derivative. Hydrolysis of the oxazolidinone ring and acetylation gave an amino compound. Oxidation of the double bond in the amino compound with OsO(4) followed by acetylation gave the amino tetraacetate and removal of the acetate groups furnished the desired aminoquercitol whose exact configuration was determined by X-ray diffraction analysis. (C) 2010 Elsevier Ltd. All rights reserved.
dc.language English
dc.publisher PERGAMON-ELSEVIER SCIENCE LTD
dc.subject Chemistry
dc.title Stereospecific synthesis of a DL-gala-aminoquercitol derivative
dc.type Article
dc.identifier.volume 66
dc.identifier.startpage 3485
dc.identifier.endpage 3489
dc.contributor.department Sakarya Üniversitesi/Eğitim Fakültesi/Matematik Ve Fen Bilimleri Eğitimi Bölümü
dc.contributor.saüauthor Kurbanoğlu, Namudar İzzet
dc.contributor.saüauthor Kılıç, Harun
dc.contributor.saüauthor Balci, Mustafa
dc.relation.journal TETRAHEDRON
dc.identifier.wos WOS:000277967400015
dc.identifier.doi 10.1016/j.tet.2010.03.028
dc.contributor.author Kurbanoğlu, Namudar İzzet
dc.contributor.author Kılıç, Harun
dc.contributor.author Balci, Mustafa


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