Chemoselective high-throughput purification mediated by solid-supported reagents: Its application to the first 6,9-disubstituted purine library synthesis

Combinatorial Chemistry and High Throughput Screening

Volumn 3, Issue 2, 2000, Pages 125-129

  Kim, Kyungjin ^a   McComas, Warren ^a  

^a HOFFMANN LA ROCHE INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

PURINE DERIVATIVE;

ALKYLATION; ARTICLE; FILTRATION; ISOMERISM; PRIORITY JOURNAL; SOLID PHASE EXTRACTION; STEREOCHEMISTRY; SYNTHESIS;

EID: 0034129902     PISSN: 13862073     EISSN: None     Source Type: Journal    
DOI: 10.2174/1386207003331779     Document Type: Article

References (18)

1. a) Reviews: Kaldor, S.W.; Siegel, M. S. Curr. Opin. Chem. Biol. 1997, 1, 101-106; b) Akelah, A.; Sherrington, D. C. Chem. Rev. 1981, 81, 557-587; c) Shuttleworth, S. J.; Allin, S. M.; Sharm, P. K. Synthesis 1997, 1217-1239, and references therein.
2. a) Reviews: Kaldor, S.W.; Siegel, M. S. Curr. Opin. Chem. Biol. 1997, 1, 101-106; b) Akelah, A.; Sherrington, D. C. Chem. Rev. 1981, 81, 557-587; c) Shuttleworth, S. J.; Allin, S. M.; Sharm, P. K. Synthesis 1997, 1217-1239, and references therein.
3. a) Reviews: Kaldor, S.W.; Siegel, M. S. Curr. Opin. Chem. Biol. 1997, 1, 101-106; b) Akelah, A.; Sherrington, D. C. Chem. Rev. 1981, 81, 557-587; c) Shuttleworth, S. J.; Allin, S. M.; Sharm, P. K. Synthesis 1997, 1217-1239, and references therein.
4. Polymeric-supported boronic acid has been used for the separation of cis-diol from isomeric cis-trans mixture. The references are as follows: a) Frechet, J. M. J. Tetrahedron 1981, 37, 663-683; b) Farrall, M. J.; Frechet, J. M. J. J. Org. Chem. 1976, 41, 3877-3882; c) Seymour, E.; Frechet, J. M. J. Tetrahedron Lett. 1976, 17, 3669-3672.
5. Polymeric-supported boronic acid has been used for the separation of cis-diol from isomeric cis-trans mixture. The references are as follows: a) Frechet, J. M. J. Tetrahedron 1981, 37, 663-683; b) Farrall, M. J.; Frechet, J. M. J. J. Org. Chem. 1976, 41, 3877-3882; c) Seymour, E.; Frechet, J. M. J. Tetrahedron Lett. 1976, 17, 3669-3672.
6. Polymeric-supported boronic acid has been used for the separation of cis-diol from isomeric cis-trans mixture. The references are as follows: a) Frechet, J. M. J. Tetrahedron 1981, 37, 663-683; b) Farrall, M. J.; Frechet, J. M. J. J. Org. Chem. 1976, 41, 3877-3882; c) Seymour, E.; Frechet, J. M. J. Tetrahedron Lett. 1976, 17, 3669-3672.
7. a) Norman, T.; Gray, N.; Koh, J.; Schultz, P. J. Am. Chem. Soc. 1996, 118, 7430-7431;
8. b) Gray, N.; Kwon, S.; Schultz, P. Tetrahedron Lett. 1997, 38, 1161-1164;
9. c) Nugiel, D.; Cornelius, L.; Corbett, J. J. Org. Chem. 1997, 62, 201-203;
10. d) Fiorini, M. T.; Abell, C.; Tetrahedron Lett. 1998, 39, 1827-1830.
11. a) Schwesinger, R. Chimia, 1985, 39, 269-272;
12. b) Xu, W.; Mohan, R.; Morrissey, M. M. Bioorg. Med. Chem. Lett. 1998, 8, 1089-1092: Polymer-supported BEMP is commercially available from Fluka.
13. Kjellberg, J.; Johansson, N. G. Nucleosides & Nucleotides, 1989, 8, 225-256, and refereces therein.
14. 6).
15. The high-throughput synthesis was done utilizing the FlexChem™ solid-phase reaction system from Robbins Scientific, Sunnyvale, CA (USA).
16. 5OCl 289.0730
17. a) Polymer-supported thiophenol resin may be purchased from Argonaut Technologies, San Carlos, CA (USA) and its preparation is not published yet. General methods to synthesize polymeric thiophenol were described in reference [2b].
18. b) Polymer-supported isocyanate resin: Rebek, J.; Brown, D.; Zimmerman, S. J. Am. Chem. Soc. 1975, 97, 4407-4408; resins are also available from Argonaut Technologies.