Açık Akademik Arşiv Sistemi

Stereospecific synthesis of N-tosyl derivatives of dihydroconduramine E-2 and ent-F-2

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dc.contributor.authors Kurbanoglu, IN; Besoluk, S; Zengin, 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, IN; Besoluk, S; Zengin, M; (2010). Stereospecific synthesis of N-tosyl derivatives of dihydroconduramine E-2 and ent-F-2. ARKIVOC, , 85-77
dc.identifier.issn 1551-7004
dc.identifier.uri https://doi.org/10.3998/ark.5550190.0011.a07
dc.identifier.uri https://hdl.handle.net/20.500.12619/44222
dc.description.abstract Conduramines, dihydroconduramines and structurally related compounds belong to an important class of glycosidase inhibitors which are essential elements of many biologically active compounds. The synthesis and characterization of N-tosyl dihydroconduramine derivatives 9a and 10a starting from cyclohexadiene were carried out in the current study. The oxazolidinone 15 was prepared by the palladium-catalyzed reaction of bis-carbamate 14, synthesized from cyclohexenediol, derived in two steps from cyclohexadiene. Hydrolysis of 15 was achieved with methanolic potassium carbonate to afford 18 and the ketalization gave 21 in good yield. Osmylation of the double bond and acid-mediated acetonide removal of 21 gave 4-methyl-N-((1S, 2R, 3S, 6S)-2,3,6-trihydroxycyclohexyl) benzenesulfonamide 9a. The epoxidation of 21 followed by acid-mediated epoxide ring opening and subsequent acetonide removal produced 4-methyl-N-((1S,2R,3R,6S)-2,3,6-trihydroxycyclohexyl) benzenesulfonamide 10a. The molecules may be evaluated for biological activity.
dc.language English
dc.publisher ARKAT USA INC
dc.subject Chemistry
dc.title Stereospecific synthesis of N-tosyl derivatives of dihydroconduramine E-2 and ent-F-2
dc.type Article
dc.identifier.startpage 77
dc.identifier.endpage 85
dc.contributor.department Sakarya Üniversitesi/Eğitim Fakültesi/Matematik Ve Fen Bilimleri Eğitimi Bölümü
dc.contributor.saüauthor Kurbanoğlu, Namudar İzzet
dc.contributor.saüauthor Beşoluk, Şenol
dc.contributor.saüauthor Zengin, Mustafa
dc.relation.journal ARKIVOC
dc.identifier.wos WOS:000282480400007
dc.identifier.doi 10.3998/ark.5550190.0011.a07
dc.identifier.eissn 1551-7012
dc.contributor.author Kurbanoğlu, Namudar İzzet
dc.contributor.author Beşoluk, Şenol
dc.contributor.author Zengin, Mustafa


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