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Article: Synthetic cyclic oligosaccharides - Syntheses and structural properties of a cyclo[(1 → 4)-α-L-rhamnopyranosyl-(1 → 4)-α-D- mannopyranosyl]trioside and -tetraoside

TitleSynthetic cyclic oligosaccharides - Syntheses and structural properties of a cyclo[(1 → 4)-α-L-rhamnopyranosyl-(1 → 4)-α-D- mannopyranosyl]trioside and -tetraoside
Authors
KeywordsCarbohydrates
Cyclodextrin analogues
Cyclooligomerizations
Glycosylations
Nanotubes
Issue Date1996
Citation
Chemistry - A European Journal, 1996, v. 2, n. 5, p. 580-591 How to Cite?
AbstractAn efficient polycondensation-cyclization approach to the synthesis of cyclodextrin analogues is demonstrated by the preparation of cyclohexaoside 1 and cyclooctaoside 2. The key intermediate, disaccharide 3, bearing the cyanoethylidene group as a glycosyl donor function and the trityloxy group as a glycosyl acceptor function was prepared in 15 steps starting from L-rhamnose and D-mannose. The crucial cyclooligomerization of the disaccharide monomer 3 was carried out in the presence of TrClO4 as a promoter with the use of ultra-dry conditions at normal concentrations. This reaction led to formation of the cyclic oligosaccharides 28 and 29 (in 34 and 31% yield, respectively), which were deprotected to afford 1 and 2, respectively. The X-ray crystal structural analysis of the cyclooctaoside 2 reveals a cylindrical shape for the cyclic oligosaccharide with C4 symmetry. Individual molecules of 2 are arranged perfectly in stacks that form nanotubes in the solid state. © VCH Verlagsgesellschaft mbH, 1996.
Persistent Identifierhttp://hdl.handle.net/10722/332286
ISSN
2023 Impact Factor: 3.9
2023 SCImago Journal Rankings: 1.058
ISI Accession Number ID

 

DC FieldValueLanguage
dc.contributor.authorAshton, Peter R.-
dc.contributor.authorBrown, Christopher L.-
dc.contributor.authorMenzer, Stephan-
dc.contributor.authorNepogodiev, Sergey A.-
dc.contributor.authorStoddart, J. Fraser-
dc.contributor.authorWilliams, David J.-
dc.date.accessioned2023-10-06T05:10:17Z-
dc.date.available2023-10-06T05:10:17Z-
dc.date.issued1996-
dc.identifier.citationChemistry - A European Journal, 1996, v. 2, n. 5, p. 580-591-
dc.identifier.issn0947-6539-
dc.identifier.urihttp://hdl.handle.net/10722/332286-
dc.description.abstractAn efficient polycondensation-cyclization approach to the synthesis of cyclodextrin analogues is demonstrated by the preparation of cyclohexaoside 1 and cyclooctaoside 2. The key intermediate, disaccharide 3, bearing the cyanoethylidene group as a glycosyl donor function and the trityloxy group as a glycosyl acceptor function was prepared in 15 steps starting from L-rhamnose and D-mannose. The crucial cyclooligomerization of the disaccharide monomer 3 was carried out in the presence of TrClO4 as a promoter with the use of ultra-dry conditions at normal concentrations. This reaction led to formation of the cyclic oligosaccharides 28 and 29 (in 34 and 31% yield, respectively), which were deprotected to afford 1 and 2, respectively. The X-ray crystal structural analysis of the cyclooctaoside 2 reveals a cylindrical shape for the cyclic oligosaccharide with C4 symmetry. Individual molecules of 2 are arranged perfectly in stacks that form nanotubes in the solid state. © VCH Verlagsgesellschaft mbH, 1996.-
dc.languageeng-
dc.relation.ispartofChemistry - A European Journal-
dc.subjectCarbohydrates-
dc.subjectCyclodextrin analogues-
dc.subjectCyclooligomerizations-
dc.subjectGlycosylations-
dc.subjectNanotubes-
dc.titleSynthetic cyclic oligosaccharides - Syntheses and structural properties of a cyclo[(1 → 4)-α-L-rhamnopyranosyl-(1 → 4)-α-D- mannopyranosyl]trioside and -tetraoside-
dc.typeArticle-
dc.description.naturelink_to_subscribed_fulltext-
dc.identifier.doi10.1002/chem.19960020518-
dc.identifier.scopuseid_2-s2.0-0001008597-
dc.identifier.volume2-
dc.identifier.issue5-
dc.identifier.spage580-
dc.identifier.epage591-
dc.identifier.eissn1521-3765-
dc.identifier.isiWOS:A1996UP33900015-

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