Issue 24, 2012

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

Abstract

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.

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

Supplementary files

Article information

Article type
Paper
Submitted
23 Feb 2012
Accepted
27 Apr 2012
First published
01 May 2012

Org. Biomol. Chem., 2012,10, 4788-4794

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

J. Karabline and M. Portnoy, Org. Biomol. Chem., 2012, 10, 4788 DOI: 10.1039/C2OB25691F

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