Regioselective reductive openings of 4,6-benzylidene acetals: Synthetic and mechanistic aspects

Carbohydrate Research

Volumn 346, Issue 12, 2011, Pages 1358-1370

  Ohlin, Markus ^a   Johnsson, Richard ^a,b   Ellervik, Ulf ^a  

^a LUND UNIVERSITY   (Sweden)

^b MCGILL UNIVERSITY   (Canada)

Author keywords

4,6 Benzylidene acetal; Boranes; Lewis acid; Mechanism; Reduction; Regioselectivity

Indexed keywords

BORON COMPOUNDS; ETHERS; MECHANISMS; REDUCTION;

4,6-BENZYLIDENE ACETAL; BENZYLIDENE ACETALS; BORANES; CARBOHYDRATE CHEMISTRY; ELECTROPHILIC SPECIES; LEWIS ACID; MECHANISTIC ASPECTS; NUCLEOPHILIC OXYGEN;

REGIOSELECTIVITY;

ACETAL DERIVATIVE; BENZYLIDENE DERIVATIVE; ETHER; LEWIS ACID; METHYL 2,3 DI O BENZYL 4,6 O (4 BROMOBENZYLIDENE) ALPHA DEXTRO GLUCOPYRANOSIDE; METHYL 2,3 DI O BENZYL 4,6 O (BENZYLIDENE 1 D) ALPHA DEXTRO GLUCOPYRANOSIDE; METHYL 2,3 DI O BENZYL 4,6 O BENZYLIDENE ALPHA DEXTRO GLUCOPYRANOSIDE; UNCLASSIFIED DRUG;

CHEMICAL STRUCTURE; ELECTROPHILICITY; NUCLEOPHILICITY; PRIORITY JOURNAL; REDUCTION; REVIEW; SYNTHESIS;

EID: 79959984073     PISSN: 00086215     EISSN: 1873426X     Source Type: Journal    
DOI: 10.1016/j.carres.2011.03.032     Document Type: Article

References (67)

1. H.M. Doukas, and T.D. Fontaine J. Am. Chem. Soc. 73 1951 5917 5918
2. E.L. Eliel, and M. Rerick J. Org. Chem. 23 1958 1088
3. E.L. Eliel, V.G. Badding, and M.N. Rerick J. Am. Chem. Soc. 84 1962 2371 2377
4. S.S. Bhattacharjee, and P.A.J. Gorin Can. J. Chem. 47 1969 1195 1206
5. A. Lipták, I. Jodál, and P. Nánási Carbohydr. Res. 44 1975 1 11
6. A. Lipták, J. Imre, J. Harangi, P. Nánási, and A. Neszmélyi Tetrahedron 38 1982 3721 3727
7. P.J. Garegg, and H. Hultberg Carbohydr. Res. 93 1981 C10 C11
8. P.J. Garegg, H. Hultberg, and S. Wallin Carbohydr. Res. 108 1982 97 101
9. M. Ek, P.J. Garegg, H. Hultberg, and S. Oscarson J. Carbohydr. Chem. 2 1983 305 311
10. D.M. Hall Carbohydr. Res. 86 1980 158 160
11. M.E. Evans Carbohydr. Res. 21 1972 473 475
12. U. Ellervik, H. Grundberg, and G. Magnusson J. Org. Chem. 63 1998 9323 9338
13. N. Chida, M. Ohtsuka, K. Nakazawa, and S. Ogawa J. Org. Chem. 56 1991 2976 2983
14. E.M. Sletten, and L.J. Liotta J. Org. Chem. 71 2006 1335 1343
15. W.A. Szarek, A. Zamojski, K.N. Tiwari, and E.R. Ison Tetrahedron Lett. 27 1986 3827 3830
16. D.M. Whitfield, C.J. Ruzicka, J.P. Carver, and J.J. Krepinsky Can. J. Chem. 65 1987 693 703
17. D. Crich, and H. Li J. Org. Chem. 65 2000 801 805
18. S. Hanessian, and N.R. Plessas J. Org. Chem. 34 1969 1035 1044
19. R.W. Binkley, G.S. Goewey, and J.C. Johnston J. Org. Chem. 49 1984 992 996
20. P. Deslongchamps, C. Moreau, D. Fréhel, and R. Chênevert Can. J. Chem. 53 1975 1204 1211
21. K.V. Rao, P.R. Patil, S. Atmakuri, and K.P.R. Kartha Carbohydr. Res. 345 2010 2709 2713
22. C.-R. Shie, Z.-H. Tzeng, C.-C. Wang, and S.-C. Hung J. Chin. Chem. Soc. 56 2009 510 523
23. K. Daragics, and P. Fügedi Tetrahedron Lett. 50 2009 2914 2916
24. S.D. Debenham, and E.J. Toone Tetrahedron: Asymmetry 11 2000 385 387
25. M.P. DeNinno, J.B. Etienne, and K.C. Duplantier Tetrahedron Lett. 36 1995 669 672
26. C.-R. Shie, Z.-H. Tzeng, S.S. Kulkarni, B.-J. Uang, C.-Y. Hsu, and S.-C. Hung Angew. Chem., Int. Ed. 44 2005 1665 1668
27. N. Tanaka, I. Ogawa, S. Yoshigase, and J. Nokami Carbohydr. Res. 343 2008 2675 2679
28. M. Oikawa, W.-C. Liu, Y. Nakai, S. Koshida, K. Fukase, and S. Kusumoto Synlett 1996 1179 1180
29. T. Ishikawa, Y. Shimizu, T. Kudoh, and S. Saito Org. Lett. 21 2003 3879 3882
30. S. Chandrasekhar, Y.R. Reddy, and C.R. Reddy Chem. Lett. 1998 1273 1274
31. C.-C. Wang, S.-Y. Luo, C.-R. Shie, and S.C. Hung Org. Lett. 4 2002 847 849
32. L. Jiang, and T.-H. Chan Tetrahedron. Lett. 39 1998 355 358
33. T. Mikami, H. Asano, and O. Mitsunobu Chem. Lett. 1987 2033 2036
34. S. Tani, S. Sawadi, M. Kojima, S. Akai, and K.-i. Sato Tetrahedron Lett. 48 2007 3103 3104
35. U. Ellervik, and G. Magnusson J. Org. Chem. 63 1998 9314 9322
36. N.E. Nifant'ev, A.S. Shashkov, Y.E. Tsvetkov, A.B. Tuzikov, I.V. Abramenko, D.F. Gluzman, and N.V. Bovin P. Kovác, Synthetic Oligosaccharides Vol. 560 1994 American Chemical Society Washington 267 275
37. N.L. Pohl, and L.L. Kiessling Tetrahedron Lett. 38 1997 6985 6988
38. A.I. Zinin, N.N. Malysheva, A.M. Shpirt, V.I. Torgov, and L.O. Kononov Carbohydr. Res. 342 2007 627 630
39. R. Johansson, and B. Samuelsson J. Chem. Soc., Chem. Commun. 1984 201 202
40. R. Johansson, and B. Samuelsson J. Chem. Soc., Perkin Trans. 1 1984 2371 2374
41. M. Ghosh, R.G. Dulina, R. Kakarla, and M.J. Sofia J. Org. Chem. 65 2000 8387 8390
42. A.A. Sherman, Y.V. Mironov, O.N. Yudina, and N.E. Nifantiev Carbohydr. Res. 338 2003 697 703
43. K. Tanaka, and K. Fukase Synlett 2007 164 166
44. J.M. Hernández-Torres, J. Achkar, and A. Wei J. Org. Chem. 69 2004 7206 7211
45. S. Deng, U. Gangadharmath, and C.-W.T. Chang J. Org. Chem. 71 2006 5179 5185
46. V. Balakumar, A. Aravind, and S. Baskaran Synlett 2004 647 650
47. M. Sakagami, and H. Hamana Tetrahedron Lett. 41 2000 5547 5551
48. R. Panchadhayee, and A.K. Misra Synlett 2010 1193 1196
49. Y. Vohra, M. Vasan, A. Venot, and G.-J. Boons Org. Lett. 10 2008 3247 3250
50. R. Johnsson, M. Ohlin, and U. Ellervik J. Org. Chem. 75 2010 8003 8011
51. P.J. Garegg S. Hanessian, Preparative Carbohydrate Chemistry 1996 Marcel Dekker New York 53 67
52. R. Johnsson, K. Mani, F. Cheng, and U. Ellervik J. Org. Chem. 71 2006 3444 3451
53. R. Johnsson, R. Cukalevski, F. Dragén, D. Ivaisevic, I. Johansson, L. Petersson, E. Elgstrand Wettergren, K.B. Yam, B. Yang, and U. Ellervik Carbohydr. Res. 343 2008 2997 3000
54. J. Kihlberg, T. Frejd, K. Jansson, and G. Magnusson Carbohydr. Res. 152 1986 113 130
55. R. Johnsson, D. Olsson, and U. Ellervik J. Org. Chem. 73 2008 5226 5232
56. T. Mukaiyama, and M. Hayashi Chem. Lett. 1974 15 16
57. S.E. Denmark, and N.G. Almstead J. Org. Chem. 56 1991 6485 6487
58. S.E. Denmark, and T.M. Willson J. Am. Chem. Soc. 111 1989 3475 3476
59. J. Derouault, P. Granger, and M.T. Forel Inorg. Chem. 16 1977 3214 3218
60. A.H. Cowley, M.C. Cushner, R.E. Davies, and P.E. Riley Inorg. Chem. 20 1981 1179 1181
61. P.R. Rablen J. Am. Chem. Soc. 119 1997 8350 8360
62. R.L. Richards, and A. Thompson J. Chem. Soc. A 1967 1244 1248
63. R.C. Corcoran Tetrahedron Lett. 31 1990 2101 2104
64. H.C. Brown, and L.T. Murray Inorg. Chem. 23 1984 2746 2753
65. B. Glavincevski, and S.K. Brownstein Can. J. Chem. 59 1981 3012 3015
66. M. Gálová Electrochim. Acta 29 1984 323 328
67. S. Saito, A. Kuroda, K. Tanaka, and R. Kimura Synlett 1996 231 233