An improved synthesis of a trifurcated newkome-type monomer and orthogonally protected two-generation dendrons.

Claudia M Cardona, Robert E Gawley

Index: J. Org. Chem. 67(4) , 1411-3, (2002)

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Abstract

The one-step synthesis of amino-polyether tri-tert-butyl ester monomer 2, by condensation of TRIS with tert-butyl acrylate, is reported. The nitrogen of the monomer can be protected with a Cbz group; subsequent removal of the tert-butyl esters with formic acid affords a triacid that is coupled to three monomers to afford an orthogonally protected two-generation, trifurcated polyether-polyamide dendron. The Cbz protecting group may be removed from the second-generation dendron without disturbing the tert-butyl esters of the periphery.