Synthesis of a β-(1→3)-D-rhamnotetraose by a one-pot, multiple radical fragmentation

Organic Letters

Volumn 8, Issue 19, 2006, Pages 4327-4330

  Crich, David ^a   Bowers, Albert A ^a  

^a UNIVERSITY OF ILLINOIS AT CHICAGO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BETA 1 3 RHAMNOTETRAOSE; BETA-1-3-RHAMNOTETRAOSE; OLIGOSACCHARIDE;

ARTICLE; CARBOHYDRATE ANALYSIS; CONFORMATION; MOLECULAR GENETICS; SYNTHESIS;

CARBOHYDRATE CONFORMATION; CARBOHYDRATE SEQUENCE; MOLECULAR SEQUENCE DATA; OLIGOSACCHARIDES;

EID: 33749013248     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol061706m     Document Type: Article

References (67)

1. (a) Hirooka, M.; Yoshimura, A.; Saito, I.; Ikawa, F.; Uemoto, Y.; Koto, S.; Takabatake, A.; Taniguchi, A.; Shinoda, Y.; Morinaga, A. Bull. Chem. Soc. Jpn. 2003, 76, 1409.
2. (b) Spitali, M.; Smith, A. R. W. J. Phytopath. 2000, 148, 563.
3. (c) Knirel, Y. A.; Shashkov, A. S.; Senchenkova, S. Y. N.; Ajiki, Y.; Fukuoka, S. Carbohydr. Res. 2002, 337, 1589.
4. (d) Cerantola, S.; Montrozier, H. Eur. J. Biochem. 1997, 246, 360.
5. (e) Winn, A. M.; Wilkinson, S. G. Carbohydr. Res. 1996, 294, 109.
6. (f) Senchenkova, S. N.; Shashkov, A. S.; Kecskes, M. L.; Ahohuendo, B. C.; Knirel, Y. A.; Rudolph, K. Carbohydr. Res. 2000, 329, 831.
7. (g) Vinogradov, E. V.; Campos-Portuguez, S.; Yokota, A.; Mayer, H. Carbohydr. Res. 1994, 261, 103.
8. (h) Vinogradov, E. V.; Shashkov, A. S.; Knirel, Y. A.; Zdorovenko, G. M.; Solyanik, L. P.; Gubanova, N. Y.; Yakovleva, L. M. Carbohydr. Res. 1991, 212, 307.
9. (i) Molinaro, A.; Silipo, A.; Lanzetta, R.; Newman, M.-A.; Dow, J. M.; Parrilli, M. Carbohydr. Res. 2003, 338, 277.
10. (j) Beynon, L. M.; Bundle, D. R.; Perry, M. B. Can. J. Chem. 1990, 68, 1456.
11. Hickman, J.; Ashwell, G. J. Biol. Chem. 1966, 241, 1424.
12. Smith, A. R. W.; Zamze, S. E.; Munro, S. M.; Carter, K. J.; Hignett, R. C. Eur. J. Biochem. 1985, 149, 73.
13. Yokota, S.; Kaya, S.; Sawada, S.; Kawamura, T.; Araki, Y.; Ito, E. Eur. J. Biochem. 1987, 167, 203.
14. Di Fabio, J. L.; Perry, M. B.; Bundle, D. R. Biochem. Cell Biol. 1987, 65, 968.
15. Morrison, I. M.; Young, R.; Perry, M. B.; Adams, G. A. Can. J. Chem. 1967, 45, 1987.
16. Perry, M. B.; Bundle, D. R. Infect. Immun. 1990, 58, 1391.
17. Dahl, K. M.; Barry, J.; DeBiasi, R. L. Clin. Infect. Dis. 2002, 35, 96.
18. (a) Fitoussi, F.; Arlet, G.; Grimont, P. A. D. J. Antimicrob. Chemother. 1995, 36, 537.
19. (b) Chaudhury, A.; Nath, G.; Tikoo, A.; Sanyal, S. C. J. Diarr. Dis. Res. 1999, 17, 85.
20. Perry, M. B.; Richards, J. C. Carbohydr. Res. 1990, 205, 371.
21. (a) Barresi, F.; Hindsgaul, O. In Modern Methods in Carbohydrate Synthesis; Khan, S. H., O'Neill, R. A., Eds.; Harwood Academic Publishers: Amsterdam, 1996; pp 251.
22. (b) Demchenko, A. V. Synlett 2003, 1225.
23. (c) Pozsgay, V. In Carbohydrates in Chemistry and Biology; Ernst, B., Hart, G. W., Sinay, P., Eds.; Wiley-VCH: Weinheim, Germany, 2000; Vol. 1, pp 319.
24. (d) Gridley, J. J.; Osborn, H. M. I. J. Chem. Soc., Perkin Trans. 1 2000, 1471.
25. (a) Crich, D.; Li, H. J. Org. Chem. 2002, 67, 4640.
26. (b) Crich, D.; Dai, Z. Tetrahedron 1999, 55, 1569.
27. (c) Crich, D.; Barba, G. R. Tetrahedron Lett. 1998, 39, 9339.
28. (d) Crich, D.; de la Mora, M. A.; Cruz, R. Tetrahedron 2002, 58, 35.
29. (e) Crich, D.; Banerjee, A. Org. Lett. 2005, 7, 1395.
30. (f) Crich, D.; Dudkin, V. J. Am. Chem. Soc. 2002, 124, 2263.
31. (g) Dudkin, V. Y.; Crich, D. Tetrahedron Lett. 2003, 44, 1787.
32. (h) Dudkin, V. Y.; Miller, J. S.; Danishefsky, S. J. J. Am. Chem. Soc. 2004, 126, 736.
33. (i) Miller, J. S.; Dudkin, V. Y.; Lyon, G. J.; Muir, T. W.; Danishefsky, S. J. Angew. Chem., Int. Ed. 2003, 42, 431.
34. (j) Nicolaou, K. C.; Mitchell, H. J.; Rodriguez, R. M.; Fylaktakidou, K. C.; Suzuki, H.; Conley, S. R. Chem. - Eur. J. 2000, 6, 3149.
35. (k) Kim, K. S.; Kang, S. S.; Seo, Y. S.; Kim, H. J.; Lee, Y. J.; Jeong, K.-S. Synlett 2003, 1311.
36. (l) Wu, X.; Schmidt, R. R. J. Org. Chem. 2004, 69, 1853.
37. (m) Kwon, Y. T.; Lee, Y. J.; Lee, K.; Kim, K. S. Org. Lett. 2004, 6, 3901.
38. (n) Tanaka, S.-I.; Takashina, M.; Tokimoto, H.; Fujimoto, Y.; Tanaka, K.; Fukase, K. Synlett 2005, 2325.
39. (a) Crich, D.; Banerjee, A.; Yao, Q. J. Am. Chem. Soc. 2004, 126, 14930.
40. (b) Crich, D.; Li, W.; Li, H. J. Am. Chem. Soc. 2004, 126, 15081.
41. (c) Crich, D.; Li, H.; Yao, Q.; Wink, D. J.; Sommer, R. D.; Rheingold, A. L. J. Am. Chem. Soc. 2001, 123, 5826.
42. Bedini, E.; Carabellese, A.; Barone, G.; Parrilli, M. J. Org. Chem. 2005, 70, 8064.
43. Crich, D.; Bowers, A. A. J. Org. Chem. 2006, 71, 3452.
44. For a previous example of a multiple radical fragmentation in oligosaccharide synthesis, see: Crich, D.; Hermann, F. Tetrahedron Lett. 1993, 34, 3385.
45. (a) Hanessian, S.; Plessas, N. R. J. Org. Chem. 1969, 34, 1035.
46. (b) Hanessian, S.; Plessas, N. R. J. Org. Chem. 1969, 34, 1045.
47. (c) Hanessian, S.; Plessas, N. R. J. Org. Chem. 1969, 34, 1053.
48. (d) Chana, J. S.; Collins, P. M.; Farnia, F.; Peacock, D. J. J. Chem. Soc., Chem. Commun. 1988, 94.
49. (e) Binkley, R. W.; Goewey, G. S.; Johnston, J. C. J. Org. Chem. 1984, 49, 992.
50. (f) Hanessian, S. Org. Synth. 1987, 65, 243.
51. (g) Hullar, T. L.; Siskin, S. B. J. Org. Chem. 1970, 35, 225.
52. Liotta, L. J.; Dombi, K. L.; Kelley, S. A.; Targontsidis, S.; Morin, A. M. Tetrahedron Lett. 1997, 38, 7833.
53. (a) Roberts, B. P.; Smits, T. M. Tetrahedron Lett. 2001, 42, 3663.
54. (b) Dang, H.-S.; Roberts, B. P.; Sekhon, J.; Smits, T. M. Org. Biomol. Chem. 2003, 1, 1330.
55. (c) Fielding, A. J.; Franchi, P.; Roberts, B. P.; Smits, T. M. J. Chem. Soc., Perkin Trans. 2 2002, 155.
56. (d) Cai, Y.; Dang, H.-S.; Roberts, B. P. J. Chem. Soc., Perkin Trans. 1 2002, 2449.
57. (e) Jeppesen, L. M.; Lundt, I.; Pedersen, C. Acta Chem. Scand. 1973, 27, 3579.
58. (a) McNulty, J.; Wilson, J.; Rochon, A. C. J. Org. Chem. 2004, 69, 563.
59. (b) Crich, D.; Bowers, A. A.; Yao, Q. Carbohydr. Res. 2006, 341, 1748.
60. Roberts, B. P.; Dang, H.-S.; Cai, Y. J. Chem. Soc., Perkin Trans. 1 2002, 2449.
61. Crich, D.; Yao, Q. Org. Lett. 2003, 5, 2189.
62. Crich, D.; Yao, Q. J. Am. Chem. Soc. 2004, 126, 8232.
63. (a) Beckwith, A. L. J.; Easton, C. J. J. Am. Chem. Soc. 1981, 103, 615.
64. (b) Rychnovsky, S. D.; Swenson, S. S. Tetrahedron 1997, 53, 16489.
65. Crich, D.; Li, W.; Li, H. J. Am. Chem. Soc. 2004, 126, 15081.
66. Utimoto, K.; Wakabayashi, Y.; Horiie, T.; Inoue, M.; Shishiyama, Y.; Obayashi, M.; Nozaki, H. Tetrahedron 1983, 39, 967.
67. That it was the residues of the nonreducing end with upfield resonances was confirmed by NOE experiments on the β-dimer 13. In the NOE spectrum, a clear correlation was observed between the cyclohexyl proton and the reducing end anomeric proton, which was further correlated to the downfield H-5 signal. The upfield H-5 multiplet correlated with the remaining anomeric peak.