Novel serine-based linker for the solid-phase synthesis of organic compounds

Tetrahedron Letters

Volumn 39, Issue 8, 1998, Pages 757-760

  Chou, Yuo Ling ^a   Morrissey, Michael M ^a   Mohan, Raju ^a  

^a BAYER AG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ACID; BASE; FLUORIDE ION; LINK PROTEIN; ORGANIC COMPOUND; RESIN;

ARTICLE; CONTROLLED STUDY; CYCLIZATION; DRUG SYNTHESIS; METHODOLOGY; NONHUMAN; ORGANIC CHEMISTRY; SOLID PHASE EXTRACTION;

EID: 0032546142     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10618-9     Document Type: Article

References (12)

1. 1. For recent reviews see (a) Balkenhohl, F.; von dem Bussche-Hunnefeld, C.; Lansky, A.; Zechel, C. Angew. Chem. Int. Ed. Engl. 1996, 35, 2288-2237.
2. (b) Bristol, James A. Tetrahedron, 1997,53, 6573-6706
3. 2. Stewart, J. M. and Young, J. D. Solid Phase Peptide Synthesis, Pierce Chemical Co., Rockford, IL 1984, pp. 9-14.
4. 3. Osborn, N. J. and Robinson, J. A. Tetrahedron, 1993,49, 2873-2884.
5. 3) 1.00 (m, 21), 3.90 (m, 2), 4.05 (m, 2), 5.10 (dd, 2), 7.05-7.40 (m, 6).
6. 5. The triisopropyl silyl group was chosen as the silyl group because of its relative stability to TFA as well as the fact that triisopropyl fluoride, the byproduct of the cleavage process, is a volatile compound and can be easily removed in vacuo.
7. 1H NMR and mass spectroscopy.
8. 7. Mohan, R; Chou, Y-L; Morrissey, M. M. Tetrahedron Lett. 1996, 23, 3963-3966.
9. 8. Valentine, J. J.; Nakanishi, S.; Hageman, D. L.; Snider, R. M.; Spencer, R. W. and Vinick, F. W. Biorganic and Med. Chem. Lett. 1992, 2, 333-338.
10. 3, dried and evaporated to afford the β-carboline compound 9 in 95% yield. NMR and mass spectral data are consistent with the product and with published data. 7
11. 10. HPLC purity determined from area of peak corresponding to correct molecular weight by LC ES/MS.
12. 8