Regioselective debenzylation of C-glycosyl compounds by boron trichloride

Carbohydrate Research

Volumn 340, Issue 3, 2005, Pages 481-487

  Xie, Juan ^a,b   Ménand, Mickaël ^a   Valéry, Jean Marc ^a  

^a Centre National de la Recherche Scientifique   (France)

^b Ecole Normale Superieure de Cachan   (France)

Author keywords

Boron trichloride; C Glycosyl compounds; Regioselective debenzylation

Indexed keywords

BENZENE; BORON; CHEMICAL REACTIONS; DERIVATIVES; ETHERS;

BENZYL ETHERS; DEBENZYLATION; DEPROTECTION;

GLUCOSE;

BORON DERIVATIVE; GLUCOSE DERIVATIVE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION KINETICS; DEBENZYLATION; DEPROTECTION REACTION; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE;

BENZYL COMPOUNDS; BORANES; CHLORIDES; ETHERS; HEXOSES;

EID: 13244267171     PISSN: 00086215     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.carres.2004.12.001     Document Type: Article

References (46)

1. T. Uchiyama, V.P. Vassilev, T. Kajimoto, W. Wong, H. Huang, C.-C. Lin, and C.-H. Wong J. Am. Chem. Soc. 117 1995 5395 5396
2. L. Cipolla, F. Nicotra, E. Vismara, and M. Guerrini Tetrahedron 53 1997 6163 6170
3. C.-H. Wong, F. Moris-Varas, S.-C. Hung, T.G. Marron, C.-C. Lin, K.W. Gong, and G. Weitz-Schmidt J. Am. Chem. Soc. 119 1997 8152 8158
4. E. Wellner, T. Gustafsson, J. Bäcklund, R. Holmdahl, and J. Kihlberg Chembiochem 1 2000 272 280
5. A. Walter, and B. Westermann Synlett 11 2000 1682 1684
6. A. Dondoni, P.P. Giovannini, and A. Marra J. Chem. Soc., Perkin Trans. 1 2001 2382 2388
7. J.D.C. Codée, G.A. van der Marel, C.A.A. van Boeckel, and J.H. van Boom Eur. J. Org. Chem. 2002 3954 3965
8. K. Maeda, T. Oishi, H. Oguri, and M. Hirama Chem. Commun. 1999 1063 1064
9. M.A. Leeuwenburgh, C. Kulker, H.S. Overkleeft, G.A. van der Marel, and J.H. van Boom Synlett 12 1999 1945 1947
10. J.S. Clark, and O. Hamelin Angew. Chem., Int. Ed. 39 2000 372 374
11. Y. Nagumo, H. Oguri, Y. Shindo, S. Sasaki, T. Oishi, M. Hirama, Y. Tomioka, M. Mizugaki, and T. Tsumuraya Bioorg. Med. Chem. Lett. 11 2001 2037 2040
12. H. Tanaka, K. Kawai, K. Fujiwara, and A. Murai Tetrahedron 58 2002 10017 10031
13. K.C. Nicolaou, C.-K. Hwang, and M.E. Duggan J. Am. Chem. Soc. 111 1989 6682 6690
14. J.D. Rainier, S.P. Allwein, and J.M. Cox J. Org. Chem. 66 2001 1380 1386
15. S.P. Allwein, J.M. Cox, B.E. Howard, H.W.B. Johnson, and J.D. Rainier Tetrahedron 58 2002 1997 2009
16. U. Majumder, J.M. Cox, and J.D. Rainier Org. Lett. 5 2003 913 916
17. W. Zheng, J.A. DeMattei, J.-P. Wu, J.J.-W. Duan, L.R. Cook, H. Oinuma, and Y. Kishi J. Am. Chem. Soc. 118 1996 7946 7968
18. K. Fujiwaraa, S. Souma, H. Mishima, and A. Murai Synlett 9 2002 1493 1495
19. C.J. Forsyth, S.F. Sabes, and R.A. Urbanek J. Am. Chem. Soc. 119 1997 8381 8382
20. M.S. Ermolenko Tetrahedron Lett. 42 2001 6679 6682
21. S. Hanessian, T.J. Liak, and D.M. Dixit Carbohydr. Res. 88 1981 C14 C19
22. For a review concerning the regioselectivity of debenzylation, see J. Staněk Jr. Top. Curr. Chem. 154 1990 211 256 and references cited therein
23. H. Hori, Y. Nishida, H. Ohrui, and H. Meguro J. Org. Chem. 54 1989 1346 1353
24. I.H. Gilbert, A.B. Holmes, and R.C. Young Tetrahedron Lett. 31 1990 2633 2634
25. D. Beaupère, I. Boutbaiba, A. Wadouachi, C. Frechou, G. Demailly, and R. Uzan New J. Chem. 16 1992 405 411
26. W.R. Kobertz, C.R. Bertozzi, and M.D. Bednarski J. Org. Chem. 61 1996 1894 1897
27. G. Yang, X. Ding, and F. Kong Tetrahedron Lett. 38 1997 6725 6728
28. K.P. Ravindranathan Kartha, M. Kiso, A. Hasegawa, and H.J. Jennings J. Carbohydr. Chem. 17 1998 811 817
29. J.R. Falck, D.K. Barma, S.K. Venkataraman, R. Baati, and C. Mioskowski Tetrahedron Lett. 43 2002 963 966
30. M. Sollogoub, S.K. Das, J.-M. Mallet, and P. Sinaÿ C.R. Acad. Sci. Paris 2 1999 441 448
31. B. Chevalier-du Roizel, E. Cabianca, P. Rollin, and P. Sinaÿ Tetrahedron 58 2002 9579 9583
32. T. Lecourt, A. Herault, A.J. Pearce, M. Sollogoub, and P. Sinaÿ Chem. Eur. J. 11 2004 2960 2971
33. J. Madsen, and M. Bols Angew. Chem., Int. Ed. 37 1998 3177 3178
34. J. Madsen, C. Viuf, and M. Bols Chem. Eur. J. 6 2000 1140 1146
35. T.W. Greene, and P.G.M. Wuts Protective Groups in Organic Synthesis 1999 Wiley-Interscience New York
36. P. Allevi, R. Cribiù, and M. Anastasia Tetrahedron Lett. 45 2004 5841 5843
37. 3 promoted debenzylation, see D.R. Williams, D.L. Brown, and J.W. Benbow J. Am. Chem. Soc. 111 1989 1923 1925
38. S. Tamura, H. Abe, A. Matsuda, and S. Shuto Angew. Chem., Int. Ed. 42 2003 1021 1023
39. F. Stolz, M. Reiner, A. Blume, W. Reutter, and R.R. Schmidt J. Org. Chem. 69 2004 665 679
40. J. Xie Eur. J. Org. Chem. 2002 3411 3418
41. M.S. Congreve, E.C. Davison, M.A.M. Fuhry, A.B. Holmes, A.N. Payne, R.A. Robinson, and S.E. Ward Synlett 9 1993 663 664
42. F. Durrat, J. Xie, and J.-M. Valéry Tetrahedron Lett. 45 2004 1477 1479
43. M.D. Lewis, J.K. Cha, and Y. Kishi J. Am. Chem. Soc. 104 1982 4976 4978
44. J. Grugier, J. Xie, I. Duarte, and J.-M. Valéry J. Org. Chem. 65 2000 979 984
45. G.G. Haraldsson, and J.E. Baldwin Tetrahedron 53 1997 215 224
46. D. Cabaret, and M. Wakselman J. Carbohydr. Chem. 10 1991 55 63