Synthesis, structure determination, and (radio-)fluorination of novel functionalized phosphanes suitable for the traceless Staudinger ligation

Tetrahedron

Volumn 67, Issue 25, 2011, Pages 4521-4529

  Mamat, Constantin ^a   Franke, Markus ^a   Peppel, Tim ^b   Köckerling, Martin ^b   Steinbach, Jörg ^a  

^a INSTITUTE OF ION BEAM PHYSICS AND MATERIALS RESEARCH   (Germany)

^b UNIVERSITY OF ROSTOCK   (Germany)

Author keywords

Bioorthogonal; P C cross coupling; Phosphane borane adduct; Radiofluorination; Staudinger ligation

Indexed keywords

PHOSPHORUS DERIVATIVE;

ARTICLE; CATALYSIS; CROSS COUPLING REACTION; CRYSTAL STRUCTURE; ESTERIFICATION; FLUORINATION; ISOTOPE LABELING; PRIORITY JOURNAL; RADIOCHEMISTRY; STAUDINGER REACTION; SYNTHESIS; TRACELESS STAUDINGER LIGATION;

EID: 79957762513     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2011.04.091     Document Type: Article

References (46)

1. M. Köhn, and R. Breinbauer Angew. Chem. 116 2004 3168 3178
2. E.M. Sletten, and C.R. Bertozzi Angew. Chem. 121 2009 7108 7133
3. R. Merkx, D.T.S. Rijkers, J. Kemmink, and R.M.J. Liskamp Tetrahedron Lett. 44 2003 4515 4518
4. M. Köhn, M. Gutierrez-Rodriguez, P. Jonkheijm, S. Wetzel, R. Wacker, H. Schroeder, H. Prinz, C.M. Niemeyer, R. Breinbauer, S.E. Szedlacsek, and H. Waldmann Angew. Chem. 115 2003 6010 6014
5. C. Mamat, M. Pretze, J. Steinbach, and F. Wuest J. Labelled Compd. Radiopharm. 52 2009 S142
6. M. Pretze, A. Flemming, M. Köckerling, and C. Mamat Z. Naturforsch. 65b 2010 1128 1136
7. M. Pretze, F. Wuest, T. Peppel, M. Köckerling, and C. Mamat Tetrahedron Lett. 51 2010 6410 6414
8. C. Mamat, A. Flemming, M. Köckerling, J. Steinbach, and F.R. Wuest Synthesis 2009 3311 3321
9. M.J. Hangauer, and C.R. Bertozzi Angew. Chem. 120 2008 2428 2431
10. J. Lahann Click Chemistry for Biotechnology and Material Science 2009 John Wiley Chichester, UK
11. C. Mamat, T. Ramenda, and F.R. Wuest Mini-Rev. Org. Chem. 6 2009 21 34
12. T. Kurpiers, and H.D. Mootz Angew. Chem. 121 2009 1757 1760
13. S. Bräse, C. Gil, K. Knepper, and V. Zimmermann Angew. Chem. 117 2005 5320 5374
14. A. Dolci, F. Dollé, S. Jubeau, F. Vaufrey, and C. Crouzel J. Labelled Compd. Radiopharm. 42 1999 975 985
15. F. Dollé Curr. Pharm. Des. 11 2005 3221 3235
16. For example: M.A. Al-Mohaissen, S.C. Pun, and J.J. Fröhlich Mini-Rev. Med. Chem. 10 2010 204 217
17. T. Gharbaoui, P.J. Skinner, Y.-J. Shin, C. Averbuj, J.K. Jung, B.R. Johnson, T. Duong, M. Decaire, J. Uy, M.C. Cherrier, P.J. Webb, S.Y. Tamura, N. Zou, N. Rodriguez, P.D. Boatman, C.R. Sage, A. Lindstrom, J. Xu, T.O. Schrader, B.M. Smith, R. Chen, J.G. Richman, D.T. Connolly, S.L. Colletti, J.R. Tata, and G. Semple Bioorg. Med. Chem. Lett. 17 2007 4914 4919
18. J.A. Joule, and K. Mills Heterocyclic Chemistry 4th ed. 2000 Blackwell Science Oxford
19. F. Nisic, M. Andreini, and A. Bernardi Eur. J. Org. Chem. 2009 5744 5751
20. A. Bianchi, A. Russo, and A. Bernardi Tetrahedron: Asymmetry 16 2005 381 386
21. A. Bianchi, and A. Bernardi J. Org. Chem. 71 2006 4565 4577
22. F. Nisic, and A. Bernardi Carbohydr. Res. 343 2008 1636 1643
23. E. Saxon, J.I. Armstrong, and C.R. Bertozzi Org. Lett. 2 2000 2141 2143
24. B.L. Nielsson, L.L. Kiessling, and R.T. Raines Org. Lett. 2 2000 1939 1941
25. B.L. Nielsson, L.L. Kiessling, and R.T. Raines Org. Lett. 3 2001 9 12
26. M.B. Soellner, A. Tam, and R.T. Raines J. Org. Chem. 71 2006 9824 9830
27. A. Tam, and R.T. Raines Bioorg. Med. Chem. 17 2009 1055 1063
28. O. David, W.J.N. Meester, H. Bieräugel, H.E. Schoemaker, H. Hiemstra, and J.H. van Maarseveen Angew. Chem. 115 2003 4509 4511
29. J. Zhang, H. Wang, and M. Xian Org. Lett. 11 2009 477 480
30. Crystallographic data for the structures in this paper have been deposited with the Cambridge Crystallographic Data Center as supplementary publication nos. CCDC-809415 (compound 3a), CCDC-809414 (compound 3m) and CCDC-809413 (compound 4). Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK, (fax: +44 (0)1223 336033 or e-mail: deposit@ccdc.cam.ac.uk).
31. K. Chen, and P.S. Conti Adv. Drug Delivery Rev. 62 2010 1005 1022
32. Z. Li, and P.S. Conti Adv. Drug Delivery Rev. 62 2010 1031 1051
33. M. Berndt, J. Pietzsch, and F. Wuest Nucl. Med. Biol. 34 2007 5 15
34. C. Hultsch, M. Berndt, R. Bergmann, and F. Wuest Appl. Radiat. Isot. 65 2007 818 826
35. P. Mäding, F. Füchtner, and F. Wüst Appl. Radiat. Isot. 63 2005 329 332
36. G. Vaidyanathan, and M.R. Zalutsky Bioconjugate Chem. 5 1994 352 356
37. H.-J. Wester, K. Hamacher, and G. Stöcklin Nucl. Med. Biol. 23 1996 365 372
38. K.A. Jacobson, D.C. Furlano, and K.L. Kirk J. Fluorine Chem. 39 1988 339 347
39. A.R. Jalilian, M. Bineshmarvasti, H. Rafii, H. Afarideh, and A. Shafiee J. Labelled Compd. Radiopharm. 44 2001 747 755
40. Decay corrected (d.c.) radiochemical yields (RCY's). Conversion determined via evaluation of radio-TLC.
41. W. Wadsak, L.-K. Mien, D.E. Ettlinger, H. Eidherr, D. Haeusler, K.-M. Sindelar, B.K. Keppler, R. Dudczak, K. Kletter, and M. Mitterhauser Nucl. Med. Biol. 34 2007 1019 1028
42. A.B. Reitz, R.W. Tuman, C.S. Marchione, A.D. Jordan, C.R. Bowden, and B.E. Maryanoff J. Med. Chem. 32 1989 2110 2116
43. C. Chiappe, D. Pieraccini, and P. Saullo J. Org. Chem. 68 2003 6710 6715
44. J.A.F. Joosten, B. Evers, R.P. van Summeren, J.P. Kamerling, and J.F.G. Vliegenthart Eur. J. Org. Chem. 18 2003 3569 3586
45. G.M. Sheldrick SHELXS/L-97, Programs for the Solution and Refinement of Crystal Structures 1997 University of Göttingen Göttingen
46. G.M. Sheldrick Acta Crystallogr. A64 2008 112 122