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Synthesis of Silicon Tracelsss Linker for Solid-Phase Reaction  

Mun Han-Seo (College of Pharmacy, Kyung Hee University)
Seong Jin-Hyun (College of Pharmacy, Kyung Hee University)
Publication Information
Archives of Pharmacal Research / v.27, no.4, 2004 , pp. 371-375 More about this Journal
Abstract
The silicon linker is the foremost traceless linker used in solid-phase reactions. Hydrogen fluo-ride (HF) or trifluoroacetic aicd (TFA) can remove the silicon linker with the silicon atom being replaced by a hydrogen atom. In this experiment, the linkers 1c and 2d, which are the most useful in solid-phase reactions, were synthesized, Linker 1c is composed of seven linearly linked carbons and linker 2d includes an oxygen atom in the linear carbon chain to increase the solvation capacity. The carboxylic acid component of linker 1c and 2d forms an amide or ester bond with resin. The synthesized linkers 1c and 2d could be utilized in constructing a chemical compound library that includes indole, benzodiazepine and phenothiazine (aromatic ring compounds).
Keywords
Combinatorial chemistry; Traceless linker; Silicon linker; Solid-phase reaction; Fischer indole synthesis; Benzodiazepine; Phenothiazine; Swelling; Solvation;
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1 Armstrong, A., Brackenridge, I., Jackson, R. F. W., and Kirk, J. M., A new method for the preparation of tertiary butyl ethers and esters. Tetrahedron Lett., 29, 2483-2486(1988)   DOI   ScienceOn
2 Hone, N. D., Davies, S. G., Devereux, N. J., Taylor, S. L., and Baxter, A. D., A highly acid labile silicon linker for solid phase synthesis. Tetrahedron Lett., 39, 897-900(1998)   DOI   ScienceOn
3 Lee, Y. H. and Silverman, R. B., Efficient solid-phase synthesis of compounds containing phenylalanine and its derivatives via side-chain attachment to the polymer support. J. Am. Chem. Soc., 121,8407-8408 (1999)   DOI   ScienceOn
4 Krchnak, M., Szabo, L., and Vagner, J., A solid phase traceless synthesis of quinoxalinones. Tetrahedron Lett., 41, 2835-2838 (2000)   DOI   ScienceOn
5 Moyer, M. P., Shiurba, J. F., and Rapoport, H., Metal-halogen exchange of bromoindoles. A route to substituted indoles. J. Org. Chem., 51, 5106-5110 (1986)
6 Holmes, C. P. and Jones, D. G., reagents for combinatorial organic synthesis: development of a new o-nitrobenzyl photolabile linker for solid phase synthesis. J. Org. Chem., 60,2318-2319 (1995)
7 Ponnusamy, E., Fotadar, U., Spisni, A., and Fiat, D., A novel method for the rapid, non-aqueous t-butoxycarbonylation of some o-labeled amino acids and O-N.M.R. parameters of the products. Synthesis, 48-49 (1986)
8 Slade, R. M., Phillips, M. A., and Berger, J. G., Application of an almost traceless linker in the synthesis of 2-alkylthiobenzimidazole combinatorial libraries. Molecular Diversity, 4, 215-219 (1998)   DOI   ScienceOn
9 Posner, G. H. and Switzer, C., Total synthesisof natural estrone and estradiol methyl ethers in extremely high enantiomeric purity via an asymmetric Michael addition to an unsaturated sulfoxide. J. Am. Chem. Soc., 108, 1239-1244(1986)   DOI
10 Morales, G. A., Corbett, J. w., and DeGrado, W. F., Solid-phase synthesis of benzopiperazinones. J. Org. Chem., 63, 1172-1177(1998)