182001-79-2Relevant articles and documents
A Convergent Synthesis of Carbohydrate-Containing Dendimers
Ashton, Peter R.,Boyd, Sue E.,Brown, Christopher L.,Jayaraman, Narayanaswamy,Nepogodiev, Sergey A.,Stoddart, J. Fraser
, p. 1115 - 1128 (2007/10/03)
The synthesis of carbohydrate-containing dendrimers has been achieved by a convergent grwoth 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. - Keywords: carbohydrates; cluster glucosides; convergent syntheses; dendrimers; neoglycoconjugates
