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A Convergent Synthesis of Carbohydrate‐Containing Dendrimers
Author(s) -
Ashton Peter R.,
Boyd Sue E.,
Brown Christopher L.,
Jayaraman Narayanaswamy,
Nepogodiev Sergey A.,
Stoddart J. Fraser
Publication year - 1996
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.19960020913
Subject(s) - dendrimer , hydroxymethyl , chemistry , branching (polymer chemistry) , amide , convergent synthesis , dispersity , derivative (finance) , peptide bond , tris , polymer chemistry , methylamine , combinatorial chemistry , stereochemistry , organic chemistry , biochemistry , financial economics , economics , enzyme
The synthesis of carbohydratecontaining 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 saccharidecontaining 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 C 3 symmetry was noted in both the 9‐mer and the 18‐mer.