Solid-phase synthesis and acidolytic degradation of sterically congested oligoether dendrons

Up to third-generation sterically crowded polyether dendrons were prepared on a solid support, using a novel building block derived from dimethyl 5-hydroxyisophthalate via O-allylation/Claisen rearrangement key steps. These dendrons underwent smooth disassembly to monomers, when subjected to acidic solution. The reason for this decomposition was traced to the increased electron density of the aromatic rings of the new monomers that destabilizes the bonds connecting the building blocks.