Synfacts 2007(4): 0438-0438  
DOI: 10.1055/s-2007-968296
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart · New York

A New Method for the Preparation of 2-Chlorotrityl Chloride Resin

Contributor(s): Yasuhiro Uozumi, Tsutomu Kimura
T.-K. Lee, S.-J. Ryoo, Y.-S. Lee*
Seoul National University, Korea
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Publikationsverlauf

Publikationsdatum:
23. März 2007 (online)

Significance

Polystyrene-supported 2-chlorotrityl chloride (2-CTC) was prepared and used as solid support for the solid-phase peptide synthesis. The reaction of 2-chlorobenzophenone 1 with PCl5 gave 1-chloro-2-[dichloro(phenyl)methyl]benzene 2 in 90% yield (eq. 1). The Friedel-Crafts reaction of compound 2 with 1% divinylbenzene-crosslinked polystyrene 3 in the presence of AlCl3 gave the polymer-supported 2-chlorotrityl alcohol 4, and the chlorination of the resulting alcohol 4 with SOCl2 gave 2-CTC resin 5 (eq. 2). Four peptide fragments (T-20 1-16, T-20 17-26, T-20 27-35, and ACP 65-74) were prepared by using the 2-CTC resin 5 with high purity.