Regioselective removal of the anomeric O-benzyl from differentially protected carbohydrates

Tetrahedron Letters

Volumn 52, Issue 49, 2011, Pages 6587-6590

  Jalsa, Nigel Kevin ^a  

^a UNIVERSITY OF THE WEST INDIES   (Trinidad and Tobago)

Author keywords

Anomeric position; Benzyl; Carbohydrates; Catalytic transfer hydrogenation; Protecting groups

Indexed keywords

BENZYL DERIVATIVE; CARBOHYDRATE; O BENZYL DERIVATIVE; O BENZYLIDENE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; HYDROGENATION; HYDROGENOLYSIS; STEREOCHEMISTRY;

EID: 80555122798     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2011.09.130     Document Type: Article

References (61)

1. A. Varki, R. Cummings, J. Esko, H. Freeze, G. Hart, and J. Marth The Essentials of Glycobiology 1999 Cold Spring Harbor Laboratory Press Cold Spring Harbor, New York
2. H. Paulsen Chem. Soc. Rev. 13 1984 15 45
3. R.R. Schmidt Angew. Chem., Int. Ed. Engl. 25 1986 212 235
4. X.M. Zhu, and R.R. Schmidt Angew. Chem., Int. Ed. 48 2009 1900 1934
5. Z.Y. Zhang, and G. Magnusson Carbohydr. Res. 295 1996 41 55
6. Y. Matsuzaki, Y. Ito, Y. Nakahara, and T. Ogawa Tetrahedron Lett. 34 1993 1061 1064
7. R. Weingart, and R.R. Schmidt Tetrahedron Lett. 41 2000 8753 8758
8. M. Nitz, and D.R. Bundle J. Org. Chem. 65 2000 3064 3073
9. K. Fukase, T. Yasukochi, Y. Nakai, and S. Kusumoto Tetrahedron Lett. 37 1996 3343 3344
10. K. Jansson, S. Ahlfors, T. Frejd, J. Kihlberg, G. Magnusson, J. Dahmén, G. Noorl, and K. Stenvall J. Org. Chem. 53 1988 5629 5647
11. J. Gigg, and R. Gigg J. Chem. Soc., C 1966 82 86
12. J.D.C. Codée, L.H. Hossain, and P.H. Seeberger Org. Lett. 7 2005 3251 3254
13. S. Dasgupta, and M. Nitz J. Org. Chem. 76 2011 1918 1921
14. B. Fraser-Reid, P. Konradsson, D.R. Mootoo, and U. Udodong J. Chem. Soc., Chem. Commun. 1988 823 825
15. P. Konradsson, D.R. Mootoo, R.E. McDevitt, and B. Fraser-Reid J. Chem. Soc., Chem. Commun. 1990 270 272
16. D.R. Mootoo, P. Konradsson, U. Udodong, and B. Fraser-Reid J. Am. Chem. Soc. 110 1988 5583 5584
17. K. Toshima, and K. Tatsuta Chem. Rev. 93 1993 1503 1531
18. P.H. Seeberger, and W.-C. Haase Chem. Rev. 100 2000 4349 4394
19. D. Kahne, S. Walker, Y. Cheng, and D. Van Engen J. Am. Chem. Soc. 111 1989 6881 6882
20. L. Yan, and D. Kahne J. Am. Chem. Soc. 118 1996 9239 9248
21. P.G.M. Wuts, and T.W. Greene Protective Groups in Organic Synthesis 4th ed. 2007 Wiley-Interscience Hoboken, New Jersey 102 120 Chapter 2
22. B. Fraser-Reid, Z. Wu, U.E. Udodong, and H.B. Ottosson J. Org. Chem. 55 1990 6068 6070
23. J. Madsen, C. Viuf, and M. Bols Chem. Eur. J. 6 2000 1140 1146
24. A. Pastore, S. Valerio, M. Adinolfi, and A. Iadonisi Chem. Eur. J. 17 2011 5881 5889
25. W. Lu, L. Navidpour, and S.D. Taylor Carbohydr. Res. 340 2005 1213 1217
26. T. Bieg, and W. Szeja Carbohydr. Res. 205 1990 C10 C11
27. T.M.K. Chiu, K. Sigillo, P.H. Gross, and A.H. Franz Synth. Commun. 37 2007 2355 2381
28. D. Crich, and H. Li J. Org. Chem. 65 2000 801 805
29. F.S. Ekholm, I.M. Mándity, F. Fülöp, and R. Leino Tetrahedron Lett. 52 2011 1839 1841
30. E. Decoster, J.-M. Lacombe, J.-L. Strebler, B. Ferrari, and A.A. Pavia J. Carbohydr. Chem. 2 1983 329 341
31. H. Hori, Y. Nishida, H. Ohrui, and H. Meguro J. Org. Chem. 54 1989 1346 1353
32. O. Martin, K.G. Kurz, and S.P. Rao J. Org. Chem. 52 1987 2922 2925
33. J. Xie, M. Menand, and J.-M. Valery Carbohydr. Res. 340 2005 481 487
34. A.J. Pearce, and P. Sinaÿ Angew. Chem., Int. Ed. 39 2000 3610 3612
35. N. Tanaka, I. Ogawa, S. Yoshigase, and J. Nokami Carbohydr. Res. 343 2008 2675 2679
36. Y. Takano, M. Habiro, M. Someya, H. Hojo, and Y. Nakahara Tetrahedron Lett. 43 2002 8395 8399
37. R.A.W. Johnstone, A.H. Wilby, and I.D. Entwistle Chem. Rev. 85 1985 129 170
38. S. Nishimura Handbook of Heterogeneous Catalytic Hydrogenation for Organic Synthesis 2001 Wiley-Interscience New York, NY
39. T. Bieg, and W. Szeja Synthesis 1985 76 77
40. L. Carpino, and A. Tunga J. Org. Chem. 51 1986 1930 1932
41. S. Ram, and R.E. Ehrenkaufer Synthesis 1988 91 95
42. B.E. Amin, G.M. Anantharamaiah, G.P. Royer, and G.E. Means J. Org. Chem. 44 1979 3442 3444
43. M.E. Jung, Y. Usui, and C.T. Vu Tetrahedron Lett. 28 1987 5977 5980
44. S. Hanessian, T.J. Liak, and B. Vanasse Synthesis 1981 396 397
45. G.M. Anantharamaiah, and K.M. Sivanandaiah J. Chem. Soc., Perkin Trans. 1 1977 490 491
46. D. Beaupere, I. Boutbaiba, G. Demailly, and R. Uzan Carbohydr. Res. 180 1988 152 155
47. A. Vincent, and J. Prunet Tetrahedron Lett. 47 2006 4075 4077
48. E. Llcer, P. Romea, and F. Urpí Tetrahedron Lett. 47 2006 5815 5818
49. V.S. Rao, and A.S. Perlin Can. J. Chem. 61 1983 652 657
50. M.K. Anwer, D.B. Sherman, and J.G. Roney J. Org. Chem. 54 1989 1284 1289
51. M. Cizmeci, A. Musavi, A. Tekin, and M. Kayahan J. Am. Oil Chem. Soc. 83 2006 1063 1068
52. T. Bieg, and S. Wieslaw Carbohydr. Res. 140 1985 C7 C8
53. M. Ohlin, R. Johnsson, and U. Ellervik Carbohydr. Res. 346 2011 1358 1370 and references therein
54. K. Daragics, P. Szabó, and P. Fügedi Carbohydr. Res. 346 2011 1633 1637 and references therein
55. J. Rujirawanich, B. Kongkathip, and N. Kongkathip Carbohydr. Res. 346 2011 927 932 and references therein
56. P. Fügedi, A. Lipták, and P. Nánási Carbohydr. Res. 80 1980 233 239
57. A. Lipták Tetrahedron Lett. 17 1976 3551 3554
58. A. Lipták, P. Fügedi, and P. Nánási Carbohydr. Res. 51 1976 C19 C21
59. A. Lipták, P. Fügedi, and P. Nánási Carbohydr. Res. 65 1978 209 217
60. A. Pastore, M. Adinolfi, A. Iadonisi, and S. Valerio Carbohydr. Res. 345 2010 1316 1323
61. P. Calinaud, and J. Gelas S. Hanessian, Preparative Carbohydrate Chemistry 1998 Marcel Dekker New York 3 33