Solid-phase system containing a trityl group, process for its preparation and its use in solid-phase reactions

摘要

The invention relates to solid-phase systems which contain a trityl group in the following general formula <IMAGE> where P is a solid support material, S is a spacer group of the type alkyl, -NH-, -NR- (urethane) or -O- (ester), R<1>, R<2> and R<3> are each one or more identical or different substituents of the type alkyl, alkoxy, dialkylamino, halogen, nitro or hydrogen, and X is a linking group of the type acylamido, acyloxy, amino, halogen, hydroxyl or phosphonate, in which acyl is the radical of a carboxylic acid or the radical RCO with R as an organic radical. The object of the present invention is to provide solid-phase systems in particular for the synthesis of peptides and glycopeptides, in which the products can be cleaved off the polymeric support selectively under such mild conditions that amino acid protective groups remain on the peptide and side reactions of the anchor compound with the peptide in solution are substantially absent. p-Methyl-substituted trityl alcohols are prepared as starting compounds for the preparation of the anchor system most successfully using organometallic compounds, preferably Grignard reagents, from aromatic esters or benzophenones. An alternative preparation is Friedel-Crafts reaction of substituted benzotrihalides or benzophenone dihalides with benzene and subsequent hydrolysis of the halides to the corresponding alcohols.