Chemoselective deprotection of acid labile primary hydroxyl protecting groups under CBr 4-photoirradiation conditions

Tetrahedron

Volumn 60, Issue 50, 2004, Pages 11465-11475

  Chen, Ming Yi ^a   Patkar, Laxmikant N ^b   Lu, Kuo Cheng ^b   Lee, Adam Shih Yuan ^c   Lin, Chun Cheng ^a,b,d  

^a NATIONAL TAIPEI UNIVERSITY OF NURSING AND HEALTH SCIENCES   (Taiwan)

^b INSTITUTE OF CHEMISTRY   (Taiwan)

^c TAMKANG UNIVERSITY   (Taiwan)

^d NATIONAL CHIAO TUNG UNIVERSITY   (Taiwan)

Author keywords

CBr 4 photoirradiation; Deprotection

Indexed keywords

BENZYLIDENE DERIVATIVE; BROMINE DERIVATIVE; CARBOHYDRATE; ETHER DERIVATIVE; HYDROXYL GROUP; METHANOL; NUCLEOSIDE;

ARTICLE; DEPROTECTION REACTION; LIGHT IRRADIANCE; PRIORITY JOURNAL; REACTION ANALYSIS;

EID: 8644268123     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2004.09.095     Document Type: Article

References (60)

1. T.W. Greene, and P.G.M. Wuts Protective Groups in Organic Synthesis 2nd ed. 1999 Wiley New York pp 113-148
2. P.J. Kocienski Protecting Groups 1994 Georg Thieme New York pp 28-42
3. M. Tandon, and T.P. Begley Synth. Commun. 27 1997 2953 2959
4. M.-Y. Chen, L.N. Patkar, M.-D. Jan, A.S.-Y. Lee, and C.-C. Lin Tetrahedron Lett. 45 2004 635 639
5. M.-Y. Chen, K.-C. Lu, A.S.-Y. Lee, and C.-C. Lin Tetrahedron Lett. 43 2002 2777 2780
6. A.S.-Y. Lee, F.-Y. Su, and Y.-C. Liao Tetrahedron Lett. 40 1999 1323 1326
7. C. Johnstone, W.J. Kerr, and J.S. Scott J. Chem. Soc. Chem. Commun. 1996 341 342
8. A. Wagner, M.P. Heitz, and C. Mioskowski Tetrahedron Lett. 31 1990 3141 3144
9. E.J. Corey, and P.L. Fuchs Tetrahedron Lett. 1972 3769 3772
10. A.S.-Y. Lee, H.-C. Yeh, and J.-J. Shie Tetrahedron Lett. 39 1998 5249 5252
11. A.S.-Y. Lee, Y.-J. Hu, and S.-F. Chu Tetrahedron 57 2001 2121 2126
12. J.S. Yadav, and B.V.S. Reddy Carbohydr. Res. 329 2000 885 888
13. J.S. Yadav, and B.V.S. Reddy Chem. Lett. 2000 566 567
14. M.-Y. Chen, and A.S.-Y. Lee J. Org. Chem. 67 2002 1384 1387
15. G. Bartoli, M. Bosco, E. Marcantoni, L. Sambri, and E. Torregiani Synlett 1998 209 211
16. J. Muzart Synthesis 1993 11 27
17. M. Lalonde, and T.H. Chan Synthesis 1985 817 845
18. For the deprotection of TBDMS group see Refs. 3b,10c, and the references cited therein.
19. T.D. Nelson, and R.D. Crouch Synthesis 1996 1031 1069
20. For recent examples (a) K. Hattori, H. Sajiki, and K. Hirota Tetrahedron 57 2001 2109 2114
21. S. Higashibayashi, K. Shinko, T. Ishizu, K. Hashimoto, H. Shirahama, and M. Nakata Synlett 2000 1306 1308
22. R. Hunter, W. Hinz, and P. Richards Tetrahedron Lett. 40 1999 3643 3646
23. K. Ramasamy, and D. Averett Synlett 1999 709 712
24. J. Farras, C. Serra, and J. Vilarrasa Tetrahedron Lett. 39 1998 327 330
25. A.H. De Groot, R.A. Dommisse, and G.L. Lemière Tetrahedron 56 2000 1541 1549
26. H. Firouzabadi, S. Etemadi, B. Karimi, and A.A. Jarrahpour Synth Commun. 29 1999 4333 4339
27. G. Maiti, and S.C. Roy Tetrahedron Lett. 38 1997 495 498
28. J. Feixas, A. Capdevila, and A. Guerrero Tetrahedron 50 1994 8539 8550
29. Y.-Y. Yang, W.-B. Yang, C.-Fen Teo, and C.-H. Lin Synlett 2000 1634 1636
30. J.F. Cormier Tetrahedron Lett. 32 1991 187 188
31. A. Kawai, O. Hara, Y. Hamada, and T. Shioiri Tetrahedron Lett. 29 1988 6331 6334
32. A.G. McInnes Can. J. Chem. 43 1965 1998 2003
33. G. Barone, E. Bedini, A. Iadonisi, E. Manzo, and M. Parrilli Synlett 2002 1645 1648
34. T. Ramalingam, R. Srinivas, B.V.S. Reddy, and J.S. Yadav Synth. Commun. 31 2001 1091 1095
35. B.V. Rao, B.V.N.B.S. Sarma, S.V. Ravindranadh, M.K. Gurjar, and M.S. Chorghade Carbohydr. Letts. 2 1997 377 380
36. J.M.G. Fernandez, C.O. Mallet, A.M. Marin, and J. Fuentes Carbohydr. Res. 274 1995 263 268
37. K.H. Park, Y.J. Yoon, and S.G. Lee Tetrahedron Lett. 35 1994 9737 9740
38. A. Khalafi-Nezad, and R.F. Alamdari Tetrahedron 57 2001 6805 6807 and references cited therein
39. C.J. Bosques, V.W.-F. Tai, and B. Imperiali Tetrahedron Lett. 42 2001 7207 7210
40. E.J. Corey, H. Cho, C. Rucker, and D.H. Hua Tetrahedron Lett. 22 1981 3455 3458
41. E.J. Corey, and A. Venkateswarlu J. Am. Chem. Soc. 94 1972 6190 6197
42. A. Rosenberg Biology of the Sialic Acids 1995 Plenum New York
43. M.J. Kiefel, and M. von Itzstein Chem. Rev. 102 2002 471 490
44. Compounds 19 and 21 have been reported (a) 19a: C.L. Mehltretter, B.H. Alexander, R.L. Mellies, and C.E. Rist J. Am. Chem. Soc. 73 1951 2425 2426
45. (b) 19b: H. Stepowska, and A. Zamojski Carbohydr. Res. 265 1994 133 137
46. (c) 19c: S. Qureshi, G. Shaw, and G.E. Burgess J. Chem. Soc., Perkin. Trans. 1 1985 1557 1563
47. (d) 19d: W.M. zu Reckendorf, N. Schultz, and R. Kreimeier Liebigs Ann. Chem. 1994 337 346
48. (e) 19e: G.W.J. Fleet, and D.R. Witty Tetrahedron: Asymmetry 1 1990 119 136
49. (f) 19g: K. Horita, S. Nagato, Y. Oikawa, and O. Yonemitsu Chem. Pharm. Bull. 37 1989 1705 1716
50. (g) 19i: J. Park, and S.F. Pedersen Tetrahedron 48 1992 2069 2080
51. (h) 21: F. Balza, and A.S. Perlin Carbohydr. Res. 107 1982 270 278
52. Compounds 25, 27, 35 and 37 have been reported. (a) 25: K. Miyajima, and K. Achiwa Chem. Pharm. Bull. 45 1997 312 320
53. (b) 27 and 35: C.-C. Lin, T.-S. Hsu, K.-C. Lu, and I.-T. Huang J. Chin. Chem. Soc. 47 2000 921 928
54. (c) See Ref. 3b.
55. S.K. Chaudhary, and O. Hernandez Tetrahedron Lett. 2 1979 95 98
56. Compounds 39, 41, 47, 49 and 51 have been reported. (a) 39: C.-C. Lin, T.-S. Hsu, K.-C. Lu, and I.-T. Huang J. Chin. Chem. Soc. 47 2000 921 928
57. (b) 41: D. Horton, and J.H. Lauterbach Carbohydr. Res. 43 1975 9 33
58. (c) 47: A. Argas-Berenguel, M. Meldal, H. Paulsen, K.J. Jensen, and K. Bock J. Chem. Soc., Perkin. Trans. 1 1994 3287 3294
59. (d) 49: H. Takahashi, H. Kittaka, and S. Ikegami J. Org. Chem. 66 2001 2705 2716
60. (e) 51: X.-A. Lu, C.-H. Chou, C.-H. Wang, and S.-C. Hung Synlett 9 2003 1364 1366