Oligosaccharide analogues of polysaccharides. Part 21. Towards new cellulose I mimics: Synthesis of dialkynyl C-glucosides of peri-substituted anthraquinone
dc.authorscopusid | 23107867800 | |
dc.authorscopusid | 7003300557 | |
dc.contributor.author | Sl M. | |
dc.contributor.author | Venanzi L.M. | |
dc.date.accessioned | 2024-08-04T19:59:07Z | |
dc.date.available | 2024-08-04T19:59:07Z | |
dc.date.issued | 2001 | |
dc.department | İnönü Üniversitesi | en_US |
dc.description.abstract | The 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.doi | 10.1002/1522-2675(20010418)84:4<939 | |
dc.identifier.endpage | 963 | en_US |
dc.identifier.issn | 0018-019X | |
dc.identifier.issue | 4 | en_US |
dc.identifier.scopus | 2-s2.0-0035043602 | en_US |
dc.identifier.scopusquality | Q2 | en_US |
dc.identifier.startpage | 939 | en_US |
dc.identifier.uri | https://doi.org/10.1002/1522-2675(20010418)84:4<939 | |
dc.identifier.uri | https://hdl.handle.net/11616/90399 | |
dc.identifier.volume | 84 | en_US |
dc.indekslendigikaynak | Scopus | en_US |
dc.language.iso | en | en_US |
dc.relation.ispartof | Helvetica Chimica Acta | en_US |
dc.relation.publicationcategory | Makale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanı | en_US |
dc.rights | info:eu-repo/semantics/openAccess | en_US |
dc.subject | Sequential coupling | en_US |
dc.subject | Acetylation | en_US |
dc.subject | Acetylene | en_US |
dc.subject | Alcohols | en_US |
dc.subject | Dimerization | en_US |
dc.subject | Hydrogen bonds | en_US |
dc.subject | Ketones | en_US |
dc.subject | Stereochemistry | en_US |
dc.subject | Synthesis (chemical) | en_US |
dc.subject | X ray analysis | en_US |
dc.subject | Cellulose | en_US |
dc.subject | anthraquinone derivative | en_US |
dc.subject | cellulose derivative | en_US |
dc.subject | glucoside | en_US |
dc.subject | article | en_US |
dc.subject | chemical modification | en_US |
dc.subject | crystal structure | en_US |
dc.subject | deacetylation | en_US |
dc.subject | structure analysis | en_US |
dc.subject | synthesis | en_US |
dc.title | Oligosaccharide analogues of polysaccharides. Part 21. Towards new cellulose I mimics: Synthesis of dialkynyl C-glucosides of peri-substituted anthraquinone | en_US |
dc.type | Article | en_US |