Synthesis of neoglycoconjugates by the desulfurative rearrangement of allylic disulfides

Journal of Organic Chemistry

Volumn 73, Issue 18, 2008, Pages 7017-7027

  Crich, David ^a   Yang, Fan ^a  

^a WAYNE STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDES; CHEMICAL REACTIONS; PHOSPHORUS COMPOUNDS; SULFUR COMPOUNDS;

ANOMERIC; AQUEOUS MEDIUM; CHEMICAL EQUATIONS; DISULFIDE EXCHANGE; GLYCOSYL; NEOGLYCOCONJUGATES; PROTECTING GROUPS; REACTION FUNCTIONS; ROOM TEMPERATURES; THIOETHER;

AMINES;

AMIDE; DISULFIDE; GLYCOPEPTIDE; SIALIC ACID DERIVATIVE; THIOL DERIVATIVE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; CHEMICAL STRUCTURE; DESULFURIZATION; ELECTROSPRAY MASS SPECTROMETRY; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOISOMERISM; SYNTHESIS;

CYSTEINE; DISULFIDES; GLYCOCONJUGATES; GLYCOSYLATION; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; ORGANOPHOSPHORUS COMPOUNDS; PEPTIDES;

EID: 52449126170     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo8015314     Document Type: Article

References (72)

1. (a) Crich, D.; Krishnamurthy, V.; Hutton, T. K. J. Am. Chem. Soc. 2006, 128, 2544-2545.
2. (b) Crich, D.; Zou, Y.; Brebion, F. J. Org. Chem. 2006, 71, 9172-9177.
3. (c) Crich, D.; Krishnamurthy, V.; Brebion, F.; Karatholuvhu, M.; Subramanian, V.; Hutton, T. K. J. Am. Chem. Soc. 2007, 129, 10282-10294.
4. (d) Li, Z.; Wang, C.; Fu, Y.; Guo, Q.-X.; Liu, L. J. Org. Chem. 2008, 73, 6127-6136.
5. (a) Paulson, J. C.; Blixt, O.; Collins, B. E. Nature Chem. Biol. 2006, 2, 238-248.
6. (b) Dwek, R. A.; Butters, T. D. Chem. Rev. 2002, 102, 283-284.
7. (c) Varki, A. Glycobiology 1993, 3, 97-130.
8. (d) Varki, A., Cummings, R., Esko, J., Freeze, H., Hart, G., Marth, J., Eds. Essentials of Glycobiology; Cold Spring Harbor Press: Cold Spring Harbor, 1999.
9. (e) Buskas, T.; Ingale, S.; Boons, G.-J. Glycobiology 2006, 16, 113R-136R.
10. (f) Werz, D. B.; Seeberger, P. H. Chem. Biol. 2007, 2, 661-691.
11. (g) Ernst, B., Hart, G. W., Sinaÿ, P., Eds. Carbohydrates in Chemistry and Biology; Wiley-VCH: Weinheim, 2000.
12. (h) Fraser-Reid, B., Kuniaki, T., Thiem, J., Eds. Glycoscience: Chemistry and Chemical Biology; Springer-Verlag: Berlin, 2001.
13. (i) Fukuda, M., Hindsgaul, O., Eds. Molecular and Cellular Glycobiology; Oxford University Press: Oxford, 2000.
14. (j) Demchenko, A. V., Ed. Frontiers in Modern Carbohydrate Chemistry; American Chemical Society: Washington, DC, 2007.
15. (k) Davis, B. G. Chem. Rev. 2002, 102, 579-601.
16. (l) Murrey, H. E.; Hsieh-Wilson, L. C. Chem. Rev. 2008, 108, 1708-1731.
17. (a) Yamamoto, N.; Tanabe, Y.; Okamoto, R.; Dawson, P. E.; Kajihara, Y. J. Am. Chem. Soc. 2008, 130, 501-510.
18. (b) Krauss, I. J.; Joyce, J. G.; Finnefrock, A. C.; Song, H. C.; Dudkin, V. Y.; Geng, X.; Warren, D. J.; Chastain, M.; Shiver, J. W.; Danishefsky, S. J. J. Am. Chem. Soc. 2007, 129, 11042-11044.
19. (c) Haase, C.; Seitz, O. Top. Curr. Chem. 2007, 267, 1-36.
20. (a) Stowell, C. P.; Lee, Y. C. Adv. Carbohydr. Chem. Biochem. 1980, 37, 225-281.
21. (b) Lee, Y. C., Lee, R. T., Eds. Neoglycoconjugates: Preparation and Applications; Academic Press: San Diego, 1994.
22. (c) Roy, R. In Carbohydrate Chemistry; Boons, G.-J., Ed.; Blackie Academic and Professional: London, 1998; pp 243-321.
23. (d) Specker, D.; Wittman, V. Top. Curr. Chem. 2007, 267, 65-108.
24. (a) Zhu, X. M.; Pachamuthu, K.; Schmidt, R. R. Org. Lett. 2004, 6, 1083-1085.
25. (b) Pachamuthu, K.; Schmidt, R. R. Chem. Rev. 2006, 106, 160-187.
26. (c) Doores, K. J.; Gamblin, D. P.; Davis, B. G. Chem. Eur. J. 2006, 12, 656-665.
27. (d) Peri, F.; Nicotra, F. Chem. Commun 2004, 623-627.
28. (e) Ohnishi, Y.; Ichikawa, M.; Ichikawa, Y. Biorg. Med. Chem. Lett. 2000, 10, 1289-1291.
29. (f) Jobron, L.; Hummel, G. Org. Lett. 2000, 2, 2265-2267.
30. (g) Cohen, S. B.; Halcomb, R. L. Org. Lett. 2001, 3, 405-407.
31. (h) Knapp, S.; Myers, D. S. J. Org. Chem. 2002, 67, 2995-2999.
32. (i) Zhu, X. M.; Schmidt, R. R. Chem. Eur. J. 2004, 10, 875-887.
33. (j) Thayer, D. A.; Yu, H. N.; Galan, M. C.; Wong, C.-H. Angew. Chem., Int. Ed. 2005, 44, 4596-4599.
34. (k) Yang, Y.-Y.; Ficht, S.; Brik, A.; Wong, C.-H. J. Am. Chem. Soc. 2007, 129, 7690-7701.
35. (l) Ficht, S.; Payne, R. J.; Brik, A.; Wong, C.-H. Angew. Chem., Int. Ed. 2007, 46, 5975-5979.
36. (m) Ichikawa, Y.; Matsukawa, Y.; Isobe, M. J. Am. Chem. Soc. 2006, 128, 3934-3938.
37. (n) Ladmiral, V.; Mantovani, G.; Clarkson, G. J.; Cauet, S.; Irwin, J. L.; Haddleton, D. M. J. Am. Chem. Soc. 2006, 128, 4823-4830.
38. (o) Hotha, S.; Kashyap, S. J. Org. Chem. 2006, 71, 364-367.
39. (p) Ichikawa, Y.; Ohara, F.; Kotsuki, H.; Nakano, K. Org. Lett. 2006, 8, 5009-5012.
40. (q) Wittrock, S.; Becker, T.; Kunz, H. Angew. Chem., Int. Ed. 2007, 46, 5226-5230.
41. (r) Ni, J.; Song, H.; Wang, Y.; Stamatos, N. M.; Wang, L.-X. Bioconjugate Chem. 2006, 17, 493-500.
42. (s) Kolomiets, E.; Johansson, E. M. V.; Renaudet, O.; Darbre, T.; Reymound, J.-L. Org. Lett. 2007, 8, 14656-11468.
43. (t) Samantaray, S.; Marathe, U.; Dasgupta, S.; Nandicoori, V. K.; Roy, R. P. J. Am. Chem. Soc. 2008, 130, 2132-2133.
44. (a) Macindoe, W. M.; van Oijen, A. H.; Boons, G.-J. Chem. Commun. 1998, 847-848.
45. (b) Gamblin, D. P.; Garnier, S. J.; Ward, N. J.; Oldham, A. J.; Fairbanks, A. J.; Davis, B. G. Org. Biomol. Chem. 2003, 1, 3642-3644.
46. (c) Gamblin, D. P.; Garnier, P.; van Kasteren, S.; Oldham, N. J.; Fairbanks, A. J.; Davis, B. G. Angew. Chem., Int. Ed. 2004, 43, 828-833.
47. (d) van Kasteren, S. I.; Kramer, H. B.; Jensen, H. H.; Campbell, S. J.; Kirkpatrick, J.; Oldham, N. J.; Anthony, D. C.; Davis, B. G. Nature 2007, 446, 1105-1109.
48. (e) Bernardes, G. J. L.; Chalker, J. M.; Errey, J. C.; Davis, B. G. J. Am. Chem. Soc. 2008, 130, 5052-5053.
49. Bernardes, G. J. L.; Grayson, E. J.; Thompson, S.; Chalker, J. M.; Errey, J. C.; El Oualid, F.; Claridge, T. D. W.; Davis, B. G. Angew. Chem., Int. Ed. 2008, 47, 2244-2247.
50. (a) Garmaise, D. I.; Uchiyama, A.; McKay, A. F. J. Org. Chem. 1962, 27, 4509-4512.
51. (b) Ferrier, R. J.; Vethaviyasar, N. J. Chem. Soc., Chem. Commun. 1970, 1385-1387.
52. (c) Hackler, R. E.; Balko, T. W. J. Org. Chem. 1973, 38, 2106-2110.
53. (d) Nakai, T.; Ari-Izumi, A. Tetrahedron Lett. 1976, 17, 2335-2338.
54. (e) Harano, K.; Ohizumi, N.; Hisano, T. Tetrahedron Lett. 1985, 26, 4203-4206.
55. (f) Harano, K.; Taguchi, T. Chem. Pharm. Bull. 1975, 23, 467-472.
56. (g) Nakai, T.; Mimura, T.; Ari-Izumi, A. Tetrahedron Lett. 1977, 2425-2428.
57. (h) Ueno, Y.; Sano, H.; Okawara, M. Tetrahedron Lett. 1980, 21, 1767-1770.
58. (i) Eto, M.; Tajiri, O.; Nakagawa, H.; Harano, K. Tetrahedron 1998, 54, 8009-8014.
59. (j) Overman, L. E.; Roberts, S. W.; Sneddon, H. F. Org. Lett. 2008, 8, 1485-1488.
60. (a) Schmidt, R. R. In Preparative Carbohydrate Chemistry; Hanessian, S., Ed.; Dekker: New York, 1997; pp 283-312.
61. (b) Schmidt, R. R.; Jung, K.-H. In Carbohydrates in Chemistry and Biology; Ernst, B., Hart, G. W., Sinaÿ, P., Eds.; Wiley-VCH: Weinheim, 2000; Vol. 1, pp 5-59.
62. The glycosylation reaction was accompanied by partial cleavage of the O-2 acetate, which was detrimental to the yield of the product. Therefore, an acetylation step was included in the workup protocol to reinstall any missing acetates.
63. (a) Danehy, J. P.; Elia, V. J. J. Org. Chem. 1972, 37, 369-373.
64. (b) Happer, D. A. R.; Mitchell, J. W.; Wright, G. J. Aust. J. Chem. 1973, 26, 121-134.
65. (c) Ichimura, A.; Nosco, D. L.; Deutsch, E. J. Am. Chem. Soc. 1983, 105, 844-850.
66. Volante, R. P. Tetrahedron Lett. 1981, 22, 3119-3122.
67. Rodriguez, E. B.; Scally, G. D.; Stick, R. V. Aust. J. Chem. 1990, 43, 1391-1405.
68. Sodeoka, M.; Yamada, H.; Shibasaki, M. J. Am. Chem. Soc. 1990, 112, 4906-4911.
69. When TLC indicated orthoester formation, TMSOTf (0.1 equiv) was added before the reaction was quenched.
70. Zibuck, R.; Streiber, J. M. J. Org. Chem. 1989, 54, 4717-4719.
71. 1e
72. Wen, S.; Guo, Z. Org. Lett. 2001, 3, 3773-3776.