File Download
There are no files associated with this item.
Links for fulltext
(May Require Subscription)
- Publisher Website: 10.1002/chem.19960020518
- Scopus: eid_2-s2.0-0001008597
- WOS: WOS:A1996UP33900015
- Find via
Supplementary
- Citations:
- Appears in Collections:
Article: Synthetic cyclic oligosaccharides - Syntheses and structural properties of a cyclo[(1 → 4)-α-L-rhamnopyranosyl-(1 → 4)-α-D- mannopyranosyl]trioside and -tetraoside
Title | Synthetic cyclic oligosaccharides - Syntheses and structural properties of a cyclo[(1 → 4)-α-L-rhamnopyranosyl-(1 → 4)-α-D- mannopyranosyl]trioside and -tetraoside |
---|---|
Authors | |
Keywords | Carbohydrates Cyclodextrin analogues Cyclooligomerizations Glycosylations Nanotubes |
Issue Date | 1996 |
Citation | Chemistry - A European Journal, 1996, v. 2, n. 5, p. 580-591 How to Cite? |
Abstract | An 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 Identifier | http://hdl.handle.net/10722/332286 |
ISSN | 2023 Impact Factor: 3.9 2023 SCImago Journal Rankings: 1.058 |
ISI Accession Number ID |
DC Field | Value | Language |
---|---|---|
dc.contributor.author | Ashton, Peter R. | - |
dc.contributor.author | Brown, Christopher L. | - |
dc.contributor.author | Menzer, Stephan | - |
dc.contributor.author | Nepogodiev, Sergey A. | - |
dc.contributor.author | Stoddart, J. Fraser | - |
dc.contributor.author | Williams, David J. | - |
dc.date.accessioned | 2023-10-06T05:10:17Z | - |
dc.date.available | 2023-10-06T05:10:17Z | - |
dc.date.issued | 1996 | - |
dc.identifier.citation | Chemistry - A European Journal, 1996, v. 2, n. 5, p. 580-591 | - |
dc.identifier.issn | 0947-6539 | - |
dc.identifier.uri | http://hdl.handle.net/10722/332286 | - |
dc.description.abstract | An 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.language | eng | - |
dc.relation.ispartof | Chemistry - A European Journal | - |
dc.subject | Carbohydrates | - |
dc.subject | Cyclodextrin analogues | - |
dc.subject | Cyclooligomerizations | - |
dc.subject | Glycosylations | - |
dc.subject | Nanotubes | - |
dc.title | Synthetic cyclic oligosaccharides - Syntheses and structural properties of a cyclo[(1 → 4)-α-L-rhamnopyranosyl-(1 → 4)-α-D- mannopyranosyl]trioside and -tetraoside | - |
dc.type | Article | - |
dc.description.nature | link_to_subscribed_fulltext | - |
dc.identifier.doi | 10.1002/chem.19960020518 | - |
dc.identifier.scopus | eid_2-s2.0-0001008597 | - |
dc.identifier.volume | 2 | - |
dc.identifier.issue | 5 | - |
dc.identifier.spage | 580 | - |
dc.identifier.epage | 591 | - |
dc.identifier.eissn | 1521-3765 | - |
dc.identifier.isi | WOS:A1996UP33900015 | - |