Development of a photolabile carbonyl-protecting group toolbox

Journal of Organic Chemistry

Volumn 76, Issue 7, 2011, Pages 2040-2048

  Yang, Haishen ^a   Zhang, Xin ^a   Zhou, Lei ^a   Wang, Pengfei ^a  

^a UNIVERSITY OF ALABAMA AT BIRMINGHAM   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

[CARBONYL; ACIDIC CONDITIONS; CARBOHYDRATE MOLECULES; CHEMICAL REAGENTS; DEPROTECTION; DEPROTECTION REACTION; DIOXOLANE; HIGH YIELD; HIGH-DENSITY; PHENYL GROUP; PHOTOCHEMICAL PROPERTIES; PHOTOLABILE PROTECTING GROUPS; PHOTOREACTIONS; PROTECTING GROUP; SITE-SPECIFIC; UV ABSORPTION; UV IRRADIATION;

ALDEHYDES; BENZENE; CARBOHYDRATES; NAPHTHALENE;

CARBONYLATION;

3 (DIMETHYLAMINO)PHENYL; ACETAL; BENZENE; CARBOHYDRATE; CARBONYL DERIVATIVE; NAPHTHALENE; PHOTOLABILE PROTECTING GROUP; SALIGENIN; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; DEPROTECTION REACTION; MICROARRAY ANALYSIS; PHOTOCHEMISTRY; PHOTOREACTIVITY; PHYSICAL CHEMISTRY; SUNLIGHT; SYNTHESIS; ULTRAVIOLET IRRADIATION;

EID: 79953184273     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo102429g     Document Type: Article

References (56)

1. Greene, T. W. and Wuts, P. G. M. Protective Groups in Organic Synthesis; Wiley: New York, 2006.
2. For reviews and monographs, see: Pillai, V. Synthesis 1980, 1
3. Binkley, R. W.; Flechtner, T. W. In Synthetic Organic Photochemistry; Horspool, W. M., Ed.; Plenum: New York, 1984; p 375.
4. Pillai, V. Org. Photochem. 1987, 9, 225
5. Givens, R. S.; Kueper, L. W., III Chem. Rev. 1993, 93, 55
6. Pirrung, M. C. Chem. Rev. 1997, 97, 473
7. Guillier, F.; Orain, D.; Bradley, M. Chem. Rev. 2000, 100, 2091
8. Bochet, C. G. J. Chem. Soc., Perkin Trans. 1 2002, 125
9. Pelliccioli, A. P.; Wirz J. Photochem. Photobiol. Sci. 2002, 1, 441
10. Dynamic studies in biology; Goeldner, M.; Givens, R. S., Eds.; Wiley-VCH: Weinheim, Germany, 2005.
11. Mayer, G.; Heckel, A. Angew. Chem., Int. Ed. 2006, 45, 4900
12. Goard, M.; Aakalu, G.; Fedoryak, O. D.; Quinonez, C.; St. Julien, J.; Poteet, S. J.; Schuman, E. M.; Dore, T. M. Chem. Biol. 2005, 12, 685
13. Plunkett, K. N.; Mohraz, A.; Haasch, R. T.; Lewis, J. A.; Moore, J. S. J. Am. Chem. Soc. 2005, 127, 14574
14. Han, G.; You, C.-C.; Kim, B.-J.; Turingan, R. S.; Forbes, N. S.; Martin, C. T.; Rotello, V. M. Angew. Chem., Int. Ed. 2006, 45, 3165
15. Kostiainen, M. A.; Smith, D. K.; Ikkala, O. Angew. Chem., Int. Ed. 2007, 46, 7600
16. Young, D. D.; Deiters, A. Angew Chem., Int. Ed. 2007, 46, 4290
17. Park, C.; Lim, J.; Yun, M.; Kim, C. Angew. Chem., Int. Ed. 2008, 47, 2959
18. Ohmuro-Matsuyama, Y.; Tatsu, Y. Angew. Chem., Int. Ed. 2008, 47, 7527
19. Muraoka, T.; Koh, C.-Y.; Cui, H.; Stupp, S. I. Angew. Chem., Int. Ed. 2009, 48, 5946
20. Kotzur, N.; Briand, B.; Beyermann, M.; Hagen, V. J. Am. Chem. Soc. 2009, 131, 16927
21. Cambridge, S.; Geissler, D.; Calegari, F.; Anastassiadis, K.; Hasan, M.; Stewart, A.; Huttner, W.; Hagen, V.; Bonhoeffer, T. Nat. Methods 2009, 6, 527
22. Young, D.; Lively, M.; Deiters, A. J. Am. Chem. Soc. 2010, 132, 6183
23. Mizukami, S.; Hosoda, M.; Satake, T.; Okada, S.; Hori, Y.; Furuta, T.; Kikuchi, K. J. Am. Chem. Soc. 2010, 132, 9524
24. Fomina, N.; McFearin, C.; Sermsakdi, M.; Edigin, O.; Almutairi, A. J. Am. Chem. Soc. 2010, 132, 9540
25. Hebert, J.; Gravel, D. Can. J. Chem. 1974, 52, 187
26. Gravel, D.; Herbert, J.; Thoraval, D. Can. J. Chem. 1983, 61, 400
27. Gravel, D.; Murray, S.; Ladouceur, G. J. Chem. Soc., Chem. Commun. 1985, 24, 1828
28. Friedrich, E.; Lutz, W.; Eichenauer, H.; Enders, D. Synthesis 1977, 12, 893
29. Hoshino, O.; Sawaki, S.; Umezawa, B. Chem. Pharm. Bull. 1979, 27, 538
30. Aurell, M. J.; Boix, C.; Ceita, M. L.; Llopis, C.; Tortajada, A.; Mestres, R. J. Chem. Res. Synop. 1995, 12, 452
31. Ceita, L.; Maiti, A. K.; Mestres, R.; Tortajada, A. J. Chem. Res. Synop. 2001, 10, 403
32. McHale, W. A.; Kutateladze, A. G. J. Org. Chem. 1998, 63, 9924
33. Lu, M.; Fedoryak, O. D.; Moister, B. R.; Dore, T. M. Org. Lett. 2003, 5, 2119
34. Blanc, A.; Bochet, C. G. J. Org. Chem. 2003, 68, 1138
35. Kantevari, S.; Narasimhaji, C. V.; Mereyala, H. B. Tetrahedron 2005, 61, 5849
36. Kostikov, A. P.; Malashikhina, N.; Popik, V. V. J. Org. Chem. 2009, 74, 1802
37. Hagen, V.; Kilic, F.; Schaal, J.; Dekowski, B.; Schmidt, R.; Kotzur, N. J. Org. Chem. 2010, 75, 2790
38. Wang, P.; Hu, H.; Wang, Y. Org. Lett. 2007, 9, 1533
39. Wang, P.; Hu, H.; Wang, Y. Org. Lett. 2007, 9, 2831
40. Wang, P.; Wang, Y.; Hu, H.; Spencer, C.; Liang, X.; Pan, L. J. Org. Chem. 2008, 73, 6152
41. Zimmerman, H. E.; Sandel, V. R. J. Am. Chem. Soc. 1963, 85, 915
42. Zimmerman, H. E.; Somasekhara, S. J. Am. Chem. Soc. 1963, 85, 922
43. Zimmerman, H. E. J. Am. Chem. Soc. 1995, 117, 8988
44. Zimmerman, H. E. J. Phys. Chem. A 1998, 102, 5616
45. The photoreactions became cleaner and more PPG reagent V could be obtained with more water as the cosolvent, albeit the yields of released carbonyl compounds were not affected. Taking into consideration of the poor solubility of the studied acetals in highly polar solvent systems, we conducted most of the photoreactions in acetonitrile/water (9:1). Photo deprotection reactions carried out in methanol did not provide cleaner reactions and better yields of released aldehydes than in acetonitrile/water (9:1). Instead some dimethyl acetal byproducts were detected in methanol. Reactions in other solvent systems were previously discussed. (5a, 5c)
46. Wang, P.; Wang, Y.; Hu, H.; Liang, X. Eur. J. Org. Chem. 2009, 208
47. Wang, P.; Mondal, M.; Wang, Y. Eur. J. Org. Chem. 2009, 2055
48. Kim, J.-H.; Huang, F.; Ly, M.; Linhardt, R. J. J. Org. Chem. 2008, 73, 9497
49. Quantum yields were determined by chemical actinometry. Defoin, A.; Defoin-Straatmann, R.; Hildenbrand, K.; Bittersmann, E.; Kreft, D.; Kuhn, H. J. J. Photochem. 1986, 33, 237
50. 2O 9:1.
51. 2O (2:3) (cell 3).
52. 4 solution in a quartz cuvette.
53. Zimmerman, H. E.; Nuss, J. M.; Tantillo, A. W. J. Org. Chem. 1988, 53, 3792
54. Zimmerman, H. E. Mol. Photochem. 1971, 3, 281
55. The structures were optimized at the HF/6-311G (d, p) level by using Gaussian 03 software: Frisch, M. J. Gaussian 03, Revision C. 02; Gaussian: Wallingford, CT, 2005
56. 3 filter solution and a Pyrex filter sleeve.