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Issue 24, 2012
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Solid-phase synthesis and acidolytic degradation of sterically congested oligoether dendrons

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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

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Article information


Submitted
23 Feb 2012
Accepted
27 Apr 2012
First published
01 May 2012

Org. Biomol. Chem., 2012,10, 4788-4794
Article type
Paper

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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