Glycosyl sulfonium ions as storable intermediates for glycosylations

Organic Letters

Volumn 13, Issue 6, 2011, Pages 1544-1547

  Nokami, Toshiki ^a   Nozaki, Yuki ^a   Saigusa, Yoshihiro ^a   Shibuya, Akito ^a   Manabe, Shino ^b   Ito, Yukishige ^b,c   Yoshida, Jun Ichi ^a  

^a KYOTO UNIVERSITY   (Japan)

^b RIKEN   (Japan)

^c JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

GLYCOSIDE; SULFONIUM DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; COMBINATORIAL CHEMISTRY; GLYCOSYLATION; NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

COMBINATORIAL CHEMISTRY TECHNIQUES; GLYCOSIDES; GLYCOSYLATION; MOLECULAR STRUCTURE; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; SULFONIUM COMPOUNDS;

EID: 79952591974     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol200242u     Document Type: Article

References (71)

1. Reviews: Boons, G. J. Tetrahedron 1996, 52, 1095
2. Seeberger, P. H.; Haase, W.-C. Chem. Rev. 2000, 100, 4349
3. Demchenko, A. V. Synlett 2003, 1225
4. Codée, J. D. C.; Litjens, R. E. J. N.; van den Bos, L. J.; Overkleeft, H. S.; van der Marel, G. A. Chem. Soc. Rev. 2005, 34, 769
5. Galoni, D. P.; Gin, D. Y. Nature 2007, 446, 1000
6. Seeberger, P. H.; Werz, D. B. Nature 2007, 446, 1046
7. Wang, Y.; Ye, X.-S. Org. Biomol. Chem. 2007, 5, 2189
8. Werz, D. B.; Ranzinger, R.; Herget, S.; Adibekian, A.; von der Lieth, C.-W.; Seeberger, P. H. ACS Chem. Biol. 2007, 2, 685
9. Seeberger, P. H. Chem. Soc. Rev. 2008, 37, 19
10. Boltje, T. J.; Buskas, T.; Boons, G. J. Nat. Chem. 2009, 1, 611
11. Nambu, H.; Nakamura, S.; Suzuki, N.; Hashimoto, S. Trends Glycosci. Glycotechnol. 2010, 22, 26
12. Ito, Y. Trends Glycosci. Glycotechnol. 2010, 22, 119
13. Mydock, L. K.; Demchenko, A. V. Org. Biomol. Chem. 2010, 8, 497
14. Crich, D. J. Carbohydr. Chem. 2002, 21, 667 and references cited therein
15. Yamago, S.; Yamada, T.; Maruyama, T.; Yoshida, J. Angew. Chem., Int. Ed. 2004, 43, 2145
16. Yamada, T.; Kinjyo, S.; Yoshida, J.; Yamago, S. Chem. Lett. 2005, 34, 1556
17. Huang, X.; Huang, L.; Wang, H.; Ye, X.-S. Angew. Chem., Int. Ed. 2004, 43, 5221
18. Wei, P.; Kerns, R. J. J. Org. Chem. 2005, 70, 4195
19. Rencurosi, A.; Lay, L.; Russo, G.; Caneva, E.; Poletti, L. Carbohydr. Res. 2006, 341, 903
20. Huang, L.; Wang, Z.; Li, X.; Ye, X.-S.; Huang, X. Carbohydr. Res. 2006, 341, 1669
21. Baek, J.-Y.; Choi, T. J.; Jeon, H.-B.; Kim., K.-S. Angew. Chem., Int. Ed. 2006, 45, 7436
22. Walvoort, M. T. C.; Ledder, G.; Mazurek, J.; Overkleeft, H. S.; Codée, J. D. C.; van der Marel, G. A. J. Am. Chem. Soc. 2009, 131, 12080
23. A recent review from the mechanistic viewpoint: Crich, D. Acc. Chem. Res. 2010, 43, 1144
24. Observation of highly reactive glycosylation intermediates other than glycosyl triflates: Gildersleeve, J.; Pascal, R. A.; Kahne, D. J. Am. Chem. Soc. 1998, 120, 5961
25. Garcia, B. A.; Gin, D. Y. J. Am. Chem. Soc. 2000, 122, 4269
26. Nokami, T.; Shibuya, A.; Tsuyama, H.; Bowers, A. A.; Crich, D.; Suga, S.; Yoshida, J. J. Am. Chem. Soc. 2007, 128, 10922
27. Nokami, T.; Tsuyama, H.; Shibuya, A.; Nakatsutsumi, T.; Yoshida, J. Chem. Lett. 2008, 37, 942
28. Nokami, T.; Shibuya, A.; Yoshida, J. Trends Glycosci. Glycotechnol. 2008, 20, 175
29. Eby, R.; Schuerch, C. Carbohydr. Res. 1974, 34, 79
30. Eby, R.; Schuerch, C. Carbohydr. Res. 1976, 50, 203
31. Maroušek, V.; Lucas, T. J.; Wheat, P. E.; Schuerch, C. Carbohydr. Res. 1978, 60, 85
32. Eby, R.; Schuerch, C. Carbohydr. Res. 1979, 77, 61
33. Eby, R. Carbohydr. Res. 1979, 70, 75
34. Eby, R.; Schuerch, C. Carbohydr. Res. 1982, 102, 131
35. Schmidt, R. R.; Rücker, E. Tetrahedron Lett. 1980, 21, 1421
36. Braccini, I.; Derouet, C.; Esnault, J.; Hervé du Penhoat, C.; Mallet, J.-M.; Michon, V.; Sinaÿ, P. Carbohydr. Res. 1993, 246, 23
37. West, A. C.; Schuerch, C. J. Am. Chem. Soc. 1973, 95, 1333
38. Kim, J.-H.; Yang, H.; Boons, G. J. Angew. Chem., Int. Ed. 2005, 44, 947
39. Kim, J.-H.; Yang, H.; Park, J.; Boons, G. J. J. Am. Chem. Soc. 2005, 127, 12090
40. Park, J.; Kawatkar, S.; Kim, J.-H.; Boons, G. J. Org. Lett. 2007, 9, 1959
41. Boltje, T. J.; Kim, J.-H.; Park, J.; Boons, G. J. Nat. Chem. 2010, 2, 552
42. Boltje, T. J.; Kim, J.-H.; Park, J.; Boons, G. J. Org. Lett. 2011, 13, 284
43. Nokami, T.; Shibuya, A.; Manabe, S.; Ito, Y.; Yoshida, J. Chem.-Eur. J. 2009, 15, 2252
44. Fascione, M. A.; Adhead, S. J.; Stalford, S. A.; Kilner, C. A.; Leach, A. G.; Turnbull, W. B. Chem. Commun. 2009, 5841
45. Stalford, S. A.; Kilner, C. A.; Leach, A. G.; Turnbull, W. B. Org. Biomol. Chem. 2009, 7, 4842
46. Geng, Y.; Ye, X.-S. Synlett 2010, 2506
47. Fascione, M. A.; Turnbull, W. B. Beilstein J. Org. Chem. 2010, 6, doi: 10.3762/bjoc.6.19. Published Online: Feb 22, 2010.
48. Examples of the synthesis of oligosaccharides containing 2-amino-2-deoxy glucose: Nicolaou, K. C.; Bockovich, N. J.; Carcanague, D. R.; Hummel, C. W.; Even, L. F. J. Am. Chem. Soc. 1992, 114, 8701
49. Ikeshita, S.; Sakamoto, A.; Nakahara, Y.; Nakahara, Y.; Ogawa, T. Tetrahedron Lett. 1994, 35, 3123
50. Solomon, D.; Fridman, M.; Zhang, J.; Baasov, T. Org. Lett. 2001, 3, 4311
51. Fridman, M.; Solomon, D.; Yogev, S.; Baasov, T. Org. Lett. 2002, 4, 281
52. Yang, F.; He, H.; Du, Y. Tetrahedron Lett. 2002, 43, 7561
53. Manabe, S.; Ishii, K.; Ito, Y. J. Org. Chem. 2007, 72, 6107
54. Yang, Y.; Li, Y.; Yu, B. J. Am. Chem. Soc. 2009, 131, 12076
55. α-Glycosyl triflate 2 is also unstable and gradually decomposes in a freezer at -80 °C.
56. Kantoci, D.; Keglevic, D.; Derome, A. E. Carbohydr. Res. 1987, 162, 227
57. Although we observed β,β-trehalose as a major product in the reaction mixture after the disappearance of glycosyl sulfonium ion 3b, β,β-trehalose might be obtained by the reaction with adventitious water during variable-temperature NMR measurement.
58. We transferred glycosyl sulfonium ion 3b from the electrolysis cell to the Schlenk tube and stored it in a freezer at -80 °C for 24 h before use.
59. Paulsen, H.; Steiger, K.-M. Carbohydr. Res. 1987, 169, 105
60. Crich, D.; Vinod, A. U. Org. Lett. 2003, 8, 1297 and references cited therein.
61. Kusumoto, S. Trends Glycosci. Glycotechnol. 2010, 22, 107
62. Wang, Z.-G.; Zhang, X.; Visser, M.; Live, D.; Zatorski, A.; Iserloh, U.; Lloyd, K. O.; Danishefsky, S. J. Angew. Chem., Int. Ed. 2001, 40, 1728
63. Matsuo, I.; Wada, M.; Manabe, S.; Yamaguchi, Y.; Otake, K.; Kato, K.; Ito, Y. J. Am. Chem. Soc. 2003, 125, 3402
64. Glycosyl sulfonium ions and related species have been paid much attention from mechanistic viewpoints: Beaver, M. G.; Billings, S. B.; Woerpel, K. A. Eur. J. Org. Chem. 2008, 771
65. Hou, D.; Taha, H. A.; Lowary, T. L. J. Am. Chem. Soc. 2009, 131, 12937
66. Yoshida, J.; Nagaki, A.; Yamada, T. Chem.-Eur. J. 2008, 14, 7450 and references cited therein
67. Suga, S.; Yamada, D.; Yoshida, J. Chem. Lett. 2010, 39, 404
68. Nagaki, A.; Kim, H.; Usutani, H.; Matsuo, C.; Yoshida, J. Org. Biomol. Chem. 2010, 8, 1212
69. Nagaki, A.; Kim, H.; Moriwaki, Y.; Matsuo, C.; Yoshida, J. Chem.-Eur. J. 2010, 16, 11167
70. Nagaki, A.; Kenmoku, A.; Moriwaki, Y.; Hayashi, A.; Yoshida, J. Angew. Chem., Int. Ed. 2010, 49, 7543
71. Nagaki, A.; Takizawa., E.; Yoshida, J. Chem.-Eur. J. 2010, 16, 14149