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Hydroxy‐Functionalized Dendritic Building Blocks
Author(s) -
Ingerl Andrea,
Neubert Ingo,
Klopsch Rainer,
Schlüter A. Dieter
Publication year - 1998
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/(sici)1099-0690(199811)1998:11<2551::aid-ejoc2551>3.0.co;2-y
Subject(s) - dendrimer , chemistry , amine gas treating , carboxylic acid , combinatorial chemistry , recrystallization (geology) , polymer , peptide synthesis , organic chemistry , peptide , paleontology , biochemistry , biology
A convenient and practical multi‐gram procedure for the synthesis of second‐ (G2; 4a , 5a , 5d ) and third‐generation (G3; 6a ) dendrons with orthogonally protected functional groups in the periphery (hydroxy) and at the focal point (carboxylic acid) is described. It uses the amply available first‐generation dendrons with amine and carboxylic ester functions ( 1 ) and tetrahydropyranyl‐protected hydroxy and carboxylic acid functions ( 2b , 3 ), respectively, which are connected via amides by peptide methods. Purification is either done by recrystallization or simple filtration through silica gel and yields the products as analytically pure materials on a several‐gram scale (even for G3). ‘The dendrons’ protective groups are proven to be orthogonal (500‐MHz NMR) which makes them useful components (building blocks) of a future dendron construction kit for a versatile synthesis of, for example, dendronized polymers.