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

Peter R. Ashton, Christopher L. Brown, Stephan Menzer, Sergey A. Nepogodiev, J. Fraser Stoddart*, David J. Williams

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

71 Scopus citations

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.

Original languageEnglish (US)
Pages (from-to)580-591
Number of pages12
JournalChemistry - A European Journal
Volume2
Issue number5
DOIs
StatePublished - 1996

Keywords

  • Carbohydrates
  • Cyclodextrin analogues
  • Cyclooligomerizations
  • Glycosylations
  • Nanotubes

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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