Quality control of solid-phase synthesis: 13C PST/MAS NMR analysis on non-destructed SynPhase lantern

Tetrahedron Letters

Volumn 47, Issue 10, 2006, Pages 1673-1677

  Arai, Takayoshi ^a   Fujiwara, Akitsugu ^a   Watanabe, Masahiko ^a   Yokoyama, Naota ^a   Fujito, Teruaki ^b   Deguchi, Kenzo ^b   Yanagisawa, Akira ^a  

^a CHIBA UNIVERSITY   (Japan)

^b JEOL LTD   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; COMBINATORIAL CHEMISTRY; CYCLOADDITION; MONITORING; POLYMERIZATION; QUALITY CONTROL; SOLID PHASE SYNTHESIS;

EID: 31944444105     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.12.128     Document Type: Article

References (26)

1. Recent representative books on combinatorial chemistry: H. Fenniri Combinatorial Chemistry 2000 Oxford University Press Oxford
2. P. Seneci Solid-Phase Synthesis and Combinatorial Technologies 2000 Wiley-Interscience New York
3. K.C. Nicolaou R. Hanko W. Hartwig Drugs, Catalysts, Materials Handbook of Combinatorial Chemistry Vols. 1 and 2 2002 Wiley-VCH Germany
4. Diversity-oriented split-pool synthesis provided a brilliant perspective on chemical genetics. See: S.L. Schreiber Bioorg. Med. Chem. 6 1998 1127 1152
5. S.L. Schreiber Science 287 2000 1964 1969
6. SynPhase lanterns are available from Mimotopes. www.mimotopes.com.
7. J. Chin, B. Fell, M.J. Shapiro, J. Tomesch, J.R. Wareing, and A.M. Bray J. Org. Chem. 62 1997 538 539
8. P. Rousselot-Pailley, N.J. Ede, and G. Lippens J. Comb. Chem. 3 2001 559 563
9. And see also A.M. Sefler, and S.W. Gerritz J. Comb. Chem. 2 2000 127 133
10. A book on the analysis methods: H. Bing Analysis and Purification Methods in Combinatorial Chemistry 2004 John Wiley & Sons Hoboken NJ
11. See also representative examples for the analyses of macroscopic solid supports: J.L. Aubagnac, C. Enjalbal, G. Subra, A.M. Bray, R. Combarieu, and J. Martinez J. Mass Spectrom. 33 1998 1094 1103
12. H.U. Gremlich, and S.L. Berets Appl. Spectrosc. 50 1996 532 536
13. All NMR experiments were performed at 298 K on a JEOL LA 400 MHz spectrometer (JEOL, Japan) equipped with a 7 mm MAS probe using a 4.5 kHz spinning rate.
14. A recent representative book on MAS/NMR: I. Ando T. Asakura Solid State NMR of Polymers 1998 Elsevier Science Amsterdam
15. HR/MAS has been typically operated using a 4 mm nanoprobe. J. Schaefer, and E.O. Stejskal Top. Carbon-13 NMR Spectrosc. 3 1979 283 324
16. C.S. Yannoni Acc. Chem. Res. 15 1982 201 208
17. R.E. Wasylishen, and C.A. Fyfe Annu. Rep. NMR Spectrosc. 12 1982 1 80
18. R.A. Komoroski High-Resolution NMR Spectroscopy of Synthetic Polymers in Bulk 1986 VCH Deerfield Bleach, FL
19. H. Saito, and I. Ando Annu. Rep. NMR Spectrosc. 21 1989 209 290
20. I. Ando, T. Yamanobe, and T. Asakura Prog. NMR Spectrosc. 22 1990 349 400
21. 13C NMR of HR/MAS is the same as with a swollen resin (SR)/MAS. See: S. Kobayashi, R. Akiyama, T. Furuta, and M. Moriwaki Molecules 2 1998 35 39
22. Fujito, T.; Deguchi, K.; Ohuchi, M.; Imanari, M.; Albright, M. J. The 20th Meeting of NMR, Tokyo, 1981, p 68.
23. M. Kanekiyo, M. Kobayashi, I. Ando, H. Kurosu, and S. Amiya Macromolecules 33 2000 7971 7976
24. The duty cycle is given as PW/(PW + PI).
25. R. Grigg, V. Sridharan, S. Suganthan, and A.W. Bridge Tetrahedron 51 1995 295 306
26. B.C. Hamper, D.R. Dukesherer, and M.S. South Tetrahedron Lett. 37 1996 3671 3674