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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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Publication details

The article was received on 23 Feb 2012, accepted on 27 Apr 2012 and first published on 01 May 2012


Article type: Paper
DOI: 10.1039/C2OB25691F
Citation: Org. Biomol. Chem., 2012,10, 4788-4794
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    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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