Phenacyl esters as a new photocleavable linker in liquid-phase chemistry

Tetrahedron Letters

Volumn 46, Issue 19, 2005, Pages 3399-3402

  Du, Li Hua ^a   Zhang, Shu Jia ^a   Wang, Yan Guang ^a  

^a ZHEJIANG UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ALIPHATIC CARBOXYLIC ACID; AMINO ACID DERIVATIVE; AROMATIC CARBOXYLIC ACID; BENZENE; ESTER DERIVATIVE; HYDROGEN; MACROGOL; METHANOL;

ARTICLE; LIQUID; MOLECULE; PHOTOCHEMISTRY; QUANTUM YIELD; ULTRAVIOLET IRRADIATION;

EID: 17144380775     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.03.071     Document Type: Article

References (44)

1. L.A. Thompson, and J.A. Ellman Chem. Rev. 96 1996 555
2. J.R. Broach, and J. Thorner Nature 384 1996 14
3. For a review see: C.G. Bochet J. Chem. Soc., Perkin Trans. 1 2002 125 142
4. R. Rodebaugh, B. Fraser-Reid, and H.M. Geysen Tetrahedron Lett. 38 1997 7653 7656
5. C.P. Holmes, and D.G. Jones J. Org. Chem. 60 1995 2318 2319
6. C.P. Holmes J. Org. Chem. 62 1997 2370 2380
7. K.C. Nicolaou, B.S. Safina, and N. Winssinger Synlett 2001 900 903
8. K.C. Nicolaou, N. Winssinger, J. Pastor, and F. Deroose J. Am. Chem. Soc. 119 1997 449 450
9. A. Routledge, C. Abell, and S. Balasubramanian Tetrahedron Lett. 38 1997 1227 1230
10. R. Glatthar, and B. Giese Org. Lett. 2 2000 2315 2317
11. K.S. Kumar, M. Roice, and V.N. Rajasekharan Pillai Tetrahedron 57 2001 3151 3158
12. D. Enders, C. Rijksen, E. Bremus-Kobberling, A. Gillner, and J. Kobberling Tetrahedron Lett. 45 2004 2839 2841
13. N.K. Terret, M. Gardner, D.W. Gordon, R.J. Kobylecki, and J. Steele Tetrahedron 51 1995 8135 8173
14. P. Lloy-Williams, F. Albericio, and E. Giralt Tetrahedron 49 1993 11065 11133
15. S. Peukert, and B. Giese J. Org. Chem. 63 1998 9045 9051
16. H.B. Lee, and S. Balasubramanian J. Org. Chem. 64 1999 3454 3460
17. M. Kessler, R. Glatthar, B. Giese, and C.G. Bochet Org. Lett. 5 2003 1179 1181
18. M. Cano, M. Ladlow, and S. Balasubramanian J. Org. Chem. 67 2002 129 135
19. K.R. Gee, L.W. Kueper III, J. Barnes, G. Dudley, and R.S. Givens J. Org. Chem. 61 1996 1228 1233
20. S.W. Wang J. Org. Chem. 41 1976 3258 3261
21. F.S. Tjoeng, and G.A. Heavner J. Org. Chem. 48 1983 355 359
22. F.S. Tjoeng, and G.A. Heavner J. Org. Chem. 48 1983 355 359
23. D. Bellof, and M. Mutter Chimia 39 1985 317 320
24. F.S. Tjoeng, J.P. Tam, and R.B. Merrifield Int. J. Pept. Protein Res. 14 1979 262 274
25. A. Banerjee, K. Lee, Q. Yu, A.G. Fang, and D.E. Falvey Tetrahedron Lett. 39 1998 4635 4638
26. A. Banerjee, and D.E. Falvey J. Org. Chem. 62 1997 6245 6251
27. A. Banerjee, K. Lee, and D.E. Falvey Tetrahedron 55 1999 12699 12710
28. A. Banerjee, and D.E. Falvey J. Am. Chem. Soc. 120 1998 2965 2966
29. P. Klan, M. Zabadal, and D. Heger Org. Lett. 2 2000 1569 1571
30. M. Zabadal, A.P. Pelliccioli, P. Klan, and J.J. Wirz J. Phys. Chem. A 105 2001 10329 10333
31. Y.J. Shang, and Y.G. Wang Tetrahedron Lett. 43 2002 2247 2249
32. M. Xia, and Y.G. Wang Tetrahedron Lett. 43 2002 7703 7705
33. X.F. Lin, J. Zhang, and Y.G. Wang Tetrahedron Lett. 44 2003 4113 4115
34. Y.G. Wang, J. Zhang, X.F. Lin, and H.F. Ding Synlett 2003 1467 1468
35. C.M. Yeh, C.L. Tung, and C.M. Sun J. Comb. Chem. 2 2000 341 348
36. C.G. Blettner, W.A. Konig, G. Quhter, W. Stenzel, and T. Schotten Synlett 1999 307 311
37. R. Racker, K. Doring, and O. Reiser J. Org. Chem. 65 2000 6932 6939
38. R. Annunziata, M. Benaglia, M. Cinquini, and F. Cozzi Chem. Eur. J. 6 2000 133 138
39. K.J. Lee, A. Angulo, P. Ghazal, and K.D. Janda Org. Lett. 1 1999 1859 1862
40. +)
41. 2 OCO), 4.63 (s, 2H), 7.22 (d, J = 10 Hz, 1H), 7.32 (d, J = 10 Hz, 1H), 7.53 (s, 1H) ppm
42. 2 OCO), 5.32 (s, 2H), 6.58 (d, J = 15 Hz, 1H), 7.24 (d, 1H), 7.36 (d, J = 10 Hz, 1H), 7.42 (d, J = 8 Hz, 2H), 7.53 (d, J = 8.5 Hz, 2H), 7.58 (s, 1H), 7.73 (d, J = 16 Hz, 1H) ppm
43. Typical procedure for the photocleavage of the model linker 1: a solution of linker 1 (100 mg) in benzene (20 mL) was irradiated in a quartz immersion well reactor using a 200 W Xenon Short Arc lamp (USHIO INC. JAPAN) between 280 nm and 366 nm (filter, UV-340, sh) for 5-8 h. Irradiation was stopped when conversation reached at least 90% (GC). Analyses were performed using TLC, GC-MS, and HPLC-MS techniques
44. 2 OCO), 7.34 (d, J = 7.9 Hz, 1H), 7.39 (dd, J = 1.5, 7.9 Hz, 1H), 7.54 (s, 1H) ppm