A convergent synthesis of carbohydrate-containing dendrimers

Peter R. Ashton, Sue E. Boyd, Christopher L. Brown, Narayanaswamy Jayaraman, Sergey A. Nepogodiev, J. Fraser Stoddart

Research output: Contribution to journalArticlepeer-review

135 Scopus citations

Abstract

The synthesis of carbohydrate-containing dendrimers has been achieved by a convergent growth approach. The synthetic strategy involves: 1) the synthesis of the triglucosylated derivative of tris(hydroxymethyl)methylamine (TRIS), 2) the introduction of a glycine-derived spacer and 3,3′-iminodipropionic acid derived branching units on to the TRIS derivative by amide bond formation, 3) condensation of the above saccharide-containing dendrons with a trifunctional 1,3,5-benzenetricarbonyl derivative, used as the core, by formation of amide bonds, and 4) deprotection of the saccharide units. A 9-mer and an 18-mer, carrying nine and eighteen saccharide units at the periphery, respectively, have been synthesized, in high yields at each step, by this synthetic strategy. By a variety of chromatographic and spectroscopic techniques, the dendrimers were shown to be structurally homogeneous, monodisperse, and error-free at all steps in their growth. These investigations were complemented by molecular modeling studies on the dendrimers. The presence of slightly distorted C3 symmetry was noted in both the 9-mer and the 18-mer.

Original languageEnglish (US)
Pages (from-to)1115-1128
Number of pages14
JournalChemistry - A European Journal
Volume2
Issue number9
DOIs
StatePublished - Dec 1 1996

Keywords

  • Carbohydrates
  • Cluster glucosides
  • Convergent syntheses
  • Dendrimers
  • Neoglycoconjugates

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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