Efficient synthesis of ß-glycosphingolipids by reaction of stannylceramides with glycosyl iodides promoted by TBAI/AW 300 molecular sieves

European Journal of Organic Chemistry

Volumn , Issue 23, 2009, Pages 3849-3852

  Morales Serna, José Antonio ^a   Díaz, Yolanda ^a   Isabel Matheu, M ^a   Castillón, Sergio ^a  

^a UNIVERSITAT ROVIRA I VIRGILI   (Spain)

Author keywords

Ethers; Glycolipids; Glycosylation; Sphingolipids; Tin

Indexed keywords

EID: 68049140929     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200900424     Document Type: Article

References (48)

1. S. Hakomori, BBA - General Subjects 2008, 1780, 325-346.
2. A. R. Todeschini, S. Hakomori, BBA - General Subjects 2008, 1780, 421-433.
3. G. Tettamanti, R. Bassi, P. Viani, L. Riboni, Biochimie 2003, 85, 423-437.
4. Y. D. Vankar, R. R. Schmidt, Chem. Soc. Rev. 2000, 29, 201-216.
5. H. Miller-Podraza, Chem. Rev. 2000, 100, 4663-4682.
6. B. Maggio, D. C. Carrer, M. L. Fanani, R. G. Oliveira, C. M. Rosetti, Curr. Opin. Colloid Interface Sci. 2004, 8, 448-458.
7. N. Taïeb, N. Yahi, J. Fantini, Adv. Drug Delivery Rev. 2004, 56, 779-794.
8. a) K. D. McReynolds, J. Gervay-Hague, Chem. Rev. 2007, 107, 1533-1552;
9. b) L. Augustin, J. Fantini, D. R. Mootoo, Bioorg. Med. Chem. 2006,14, 1182-1188;
10. c) S. S. Rawat, B. T. Johnson, A. Puri, Biosci. Rep. 2005, 25, 329-343.
11. a) A. R. Howell, R. C. So, S. K. Richardson, Tetrahedron 2004, 60, 11327-11347;
12. b) S. Brodesser, P. Sawatzki, T. Kolter, Eur. J. Org. Chem. 2003, 2021-2034;
13. R. I. Duelos Jr, Chem. Phys. Lipids 2001, 111, 111-138.
14. a) T. J. Martin, R. R. Schmidt, Tetrahedron Lett. 1992, 33, 6123-6126;
15. b) R. R. Schmidt, P. Zimmermann, Tetrahedron Lett. 1986, 27, 481-484;
16. c) R. R. Schmidt, P. Zimmerman, An-gew. Chem. Int. Ed, Engl, 1986, 25, 725-726.
17. K. C. Nicolaou, J. Li, G. Zenke, Heb. Chim. Acta 2000, 83, 1977-2006.
18. a) P. Stallforth, A. Adibekian, P. H. Seeberger, Org. Lett. 2008, 10, 1573-1576;
19. b) N. Ding, Ch. Li, Y. Liu, Z. Zhang, Y. Li, Carbohydr. Res. 2007, 342, 2003-2013.
20. For a review on O-glycosylation of sphingosine and ceramides, see: J. A. Morales-Serna, O. Boutureira, Y. Díaz, M. I. Matheu, S. Castillón, Carbohydr. Res. 2007, 342, 1595-1612.
21. a) R. Polt, L. Szabo, J. Treiberg, Y. Li, V. J. Hruby, J. Am. Chem. Soc. 1992, 114, 10249-10258;
22. b) R. R. Schmidt, P. Zimmermann, Angew. Chem. Int. Ed. Engl. 1986, 25, 725-726.
23. M. E. Rerek, H.-C. Chen, B. Markovic, D. Van Wyck, P. Garidel, R. Mendelsohn, D. J. Moore, J. Phys. Chem. B 2001, 105, 9355-9362.
24. O. Boutureira, J. A. Morales-Serna, Y. Díaz, M. I. Matheu, S. Castillón, Eur. J. Org. Chem. 2008, 1851-1854.
25. a) J. A. Morales-Serna, O. Boutureira, Y. Diaz, M. I. Matheu, S. Castillón, Org. Biomol. Chem. 2008, (5, 443-446;
26. b) J. A. Mo-rales-Serna, Y. Díaz, M. I. Matheu, S. Castillón, Org. Biomol. Chem. 2008, 6, 3831-3836.
27. For a recent review on orthoesters, see: a) B. Fraser-Raid, J. C. López, Handbook of Chemical Glycosilation, VCH, Weinheim, 2008, pp. 381-415;
28. b) F. Kong, Carbohydr. Res. 2006, 342, 345-373.
29. a) W. Wang, F. Kong, Tetrahedron Lett. 2002, 39, 1937-1940;
30. b) J. Gass, M. Strobl, A. Loibner, P. Kosma, U. Zahringer, Carbohydr. Res. 1993, 244, 69-84;
31. c) T. Ogawa, K. Beppu, S. Nakabayashi, Carbohydr. Res. 1981, 93, C6-C9.
32. J. C. López, A. Agocs, C. Uriel, A. M. Gómez, B. Fraser-Reid, Chem. Commun. 2005, 5088-5090.
33. F. Mathew, M. Mach, K. C. Hazen, B. Fraser-Reid, Synlett 2003, 1319-1322.
34. B. Fraser-Reid, S. R. Chaudhuri, K. N. Jayaprakash, J. Lu, Ch. V. S. Ramamurty, J. Org. Chem. 2008, 73, 9732-9743.
35. G. Sureshkumar, S. Hotha, Chem. Commun. 2008, 4282-4284.
36. a) A. Ravidà, X. Liu, L. Kovacs, P. H. Seeberger, Org. Lett. 2006, 8, 1815-1818.
37. M. Adinolfi, G. Barone, A. Iadonisi, M. Schiattarella, Org. Lett. 2003, 5, 987-989.
38. M. Adinolfi, A. Iadonisi, A. Ravidà, M. Schiattarella, J. Org. Chem. 2005, 70, 5316-5319.
39. a) W. Du, J. Gervay-Hague, Org. Lett. 2005, 7, 2063-2065;
40. b) W. Du, S. S. Kulkarni, J. Gervay-Hague, Chem. Commun. 2007, 2336-2338.
41. a) S. J. Danishefsky, J. Gervay, J. M. Peterson, F. E. McDonald, K. Koseki, D. A. Griffith, T. Oriyama, S. P. Marsden, J. Am. Chem. Soc. 1995, 117, 1940-1953;
42. b) K. K.-C. Liu, S. J. Dani- shefsky, J. Org. Chem. 1994, 59, 1895-1897;
43. c) K. K.-C. Liu, S. J. Danishefsky, J. Am. Chem. Soc. 1993, 115, 4933-4934.
44. a) M. J. Hadd, J. Gervay, Carbohydr. Res. 1999, 320, 61-69;
45. b) J. Gervay, M. J. Hadd, J. Org. Chem. 1997, 62, 6961-6967.
46. a) Ch. Xia, Q. Yao, J. Schümann, E. Rossy, W. Chen, L. Zhu, W. Zhang, G. De Libero, P. G. Wang, Bioorg. Med. Chem. Lett. 2006, 16, 2195-2199;
47. b) Q. Yao, J. Song, Ch. Xia, W Zhang, P. G. Wang, Org. Lett. 2006, 8, 911-914;
48. D. Zhou, J. Mattner, C. Cantu III, N. Schrantz, N. Yin, Y Gao, Y. Sagiv, K. Hudspeth, Y.-P. Wu, T. Yamashita, S. Teneberg, D. Wang, R. L. Proia, S. B. Levery, P. B. Savage, L. Teyton, A. Bendelac, Science 2004, 306, 1786-1789.