Oligosaccharide analogues of polysaccharides. Part 21. Towards new cellulose I mimics: Synthesis of dialkynyl C-glucosides of peri-substituted anthraquinone

Basit Öğe Kaydı
dc.authorscopusid23107867800
dc.authorscopusid7003300557
dc.contributor.authorSl M.
dc.contributor.authorVenanzi L.M.
dc.date.accessioned2024-08-04T19:59:07Z
dc.date.available2024-08-04T19:59:07Z
dc.date.issued2001
dc.departmentİnönü Üniversitesien_US
dc.description.abstractThe bis-C-glucoside 2 has been synthesised as the first representative of a series of templated glucosides and cellooligosaccharides that mimick part of the unit cell of cellulose I. As expected, there are, at best, weakly persistent H-bonds between the two glucosyl residues in (D 6)DMSO and (D 7)DMF solution. The acetylated oct-1-ynitol 7 and deca-1,3-diynitol 12 were prepared from the gluconolactone 5 (Scheme 1). Coupling of 12 to Phi and 2-iodothiophene yielded 13 and 14, respectively, while dimerisation of the benzylated and acetylated deca-1,3-diynitols 10 and 12 afforded the bis-C-glucosyloctatetrayne 15 and the less stable 16, respectively. The 2-glucosylthiophene 17 was obtained by treating the C-silylated deca-1,3-diynitol 9 with Na 2S. Cross-coupling of (trimethylsilyl)acetylene (TMSA) with 1,8-bis(triflyloxy)-9,10-anthraquinone (20) at elevated temperature gave the dialkynylated 21; its structure was established by X-ray analysis (Scheme 2). Sequential coupling of 6 or 7 and TMSA to 20 gave the symmetric dialkyne 21, the mixed dialkynes 23 (from 6) and 25 (from 7), and the symmetric diglucoside 36 (from 7) in modest yields; a stepwise coupling to the acetylated monotriflate 28 proved advantageous. It led to the oct-1-ynitol 29 and the deca-1,3-diynitol 33 that were transformed into the triflates 30 and 34, respectively. Coupling of the triflate 34 to the oct-1-ynitol 7 gave the unsymmetric bis-C-glucoside 35; this was obtained in higher yields by coupling the triflate 30 to the deca-1,3-diynitol 12. Coupling of the bistriflate 20 with either 7 or 12 afforded the symmetric bis-C-glucosides 36 and 37, respectively. Deacetylation (KCN in MeOH) of 35-37 provided the unsymmetric bis-C-glucoside 2 and the symmetric analogues 3 and 4.en_US
dc.identifier.doi10.1002/1522-2675(20010418)84:4<939
dc.identifier.endpage963en_US
dc.identifier.issn0018-019X
dc.identifier.issue4en_US
dc.identifier.scopus2-s2.0-0035043602en_US
dc.identifier.scopusqualityQ2en_US
dc.identifier.startpage939en_US
dc.identifier.urihttps://doi.org/10.1002/1522-2675(20010418)84:4<939
dc.identifier.urihttps://hdl.handle.net/11616/90399
dc.identifier.volume84en_US
dc.indekslendigikaynakScopusen_US
dc.language.isoenen_US
dc.relation.ispartofHelvetica Chimica Actaen_US
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanıen_US
dc.rightsinfo:eu-repo/semantics/openAccessen_US
dc.subjectSequential couplingen_US
dc.subjectAcetylationen_US
dc.subjectAcetyleneen_US
dc.subjectAlcoholsen_US
dc.subjectDimerizationen_US
dc.subjectHydrogen bondsen_US
dc.subjectKetonesen_US
dc.subjectStereochemistryen_US
dc.subjectSynthesis (chemical)en_US
dc.subjectX ray analysisen_US
dc.subjectCelluloseen_US
dc.subjectanthraquinone derivativeen_US
dc.subjectcellulose derivativeen_US
dc.subjectglucosideen_US
dc.subjectarticleen_US
dc.subjectchemical modificationen_US
dc.subjectcrystal structureen_US
dc.subjectdeacetylationen_US
dc.subjectstructure analysisen_US
dc.subjectsynthesisen_US
dc.titleOligosaccharide analogues of polysaccharides. Part 21. Towards new cellulose I mimics: Synthesis of dialkynyl C-glucosides of peri-substituted anthraquinoneen_US
dc.typeArticleen_US

Dosyalar

Koleksiyon

Scopus İndeksli Yayınlar Koleksiyonu