An improved synthesis of a trifurcated newkome-type monomer and orthogonally protected two-generation dendrons.
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.
Cardona
Claudia M
CM
Department of Chemistry and NIEHS Marine and Freshwater Biomedical Sciences Center, University of Miami, P.O. Box 249118, Coral Gables, Florida 33124-0431, USA.
Gawley
Robert E
RE
D000588:Amines / Q000737:chemistry; D002384:Catalysis; D002625:Chemistry, Organic / Q000379:methods; D002855:Chromatography, Thin Layer; D004952:Esters / Q000138:chemical synthesis* / Q000737:chemistry*; D004987:Ethers / Q000138:chemical synthesis* / Q000737:chemistry*; D005561:Formates / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D011108:Polymers / Q000138:chemical synthesis* / Q000737:chemistry*
D000588:Amines; D004952:Esters; D004987:Ethers; D005561:Formates; D011108:Polymers; C018241:carbobenzoxy chloride