Stable spiro-endoperoxides by sunlight-mediated photooxygenation of 1,2-O-alkylidene-5(E)-eno-5,6,8-trideoxy-?-D-xylo-oct-1,4-furano-7-uloses

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dc.contributor.authorÇetin F.
dc.contributor.authorYenil N.
dc.contributor.authorYüceer L.
dc.date.accessioned2019-10-27T08:59:12Z
dc.date.available2019-10-27T08:59:12Z
dc.date.issued2005
dc.departmentEge Üniversitesien_US
dc.description.abstractSunlight-mediated photooxygenation of 3-O-acetyl and 3-O-methyl derivatives of 1,2-O-alkylidene-5(E)-eno-5,6,8-trideoxy-?-D-xylo-oct-1,4-furano-7- uloses (1a-e) in carbon tetrachloride solution gave stable 4,7-epidioxy derivatives in 4R (2a-e) and 4S (3a-e) configurations. The presence of an endo alkyl, on the 1,2-O-alkylidene group and its size, resulted in an increase of the yield of the 4S isomers. 3-O-Acetyl derivatives yielded products as a mixture of C-7 anomers, whereas 3-O-methyl derivatives gave pure single stereoisomers. © 2005 Elsevier Ltd. All rights reserved.en_US
dc.description.sponsorshipSupport from Ege and Celal Bayar Universities is gratefully acknowledged. One of the authors (Fatma Çetin) is indebted to receive a grant from TUBITAK (Scientific and Technical Research Council of Turkey). We are also grateful to Dr. Hassan Oulyadi of Lab.des Fonctions Azotées et Oxygénées Complexes, IRCOF, Cedex, France, for the 600 MHz NOESY spectra of some of the compounds and discussions. --en_US
dc.identifier.doi10.1016/j.carres.2005.09.006en_US
dc.identifier.endpage2589en_US
dc.identifier.issn0008-6215
dc.identifier.issue17en_US
dc.identifier.pmid16182263en_US
dc.identifier.scopusqualityQ2en_US
dc.identifier.startpage2583en_US
dc.identifier.urihttps://doi.org/10.1016/j.carres.2005.09.006
dc.identifier.urihttps://hdl.handle.net/11454/27717
dc.identifier.volume340en_US
dc.indekslendigikaynakScopusen_US
dc.indekslendigikaynakPubMeden_US
dc.language.isoenen_US
dc.relation.ispartofCarbohydrate Researchen_US
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanıen_US
dc.rightsinfo:eu-repo/semantics/closedAccessen_US
dc.subjectAntibioticsen_US
dc.subjectAntimalarial drugsen_US
dc.subjectEndoperoxidesen_US
dc.subjectFurano sugarsen_US
dc.subjectSpiroketalsen_US
dc.titleStable spiro-endoperoxides by sunlight-mediated photooxygenation of 1,2-O-alkylidene-5(E)-eno-5,6,8-trideoxy-?-D-xylo-oct-1,4-furano-7-ulosesen_US
dc.typeArticleen_US

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