'Armed-disarmed' glycosidation strategy based on glycosyl donors and acceptors carrying phosphoroamidate as a leaving group: A convergent synthesis of globotriaosylceramide

Tetrahedron Letters

Volumn 38, Issue 52, 1997, Pages 8969-8972

  Hashimoto, Shun Ichi ^a   Sakamoto, Hiroki ^a   Honda, Takeshi ^b,c   Abe, Hiroshi ^a   Nakamura, Sei Ichi ^a   Ikegami, Shiro ^b  

^a HOKKAIDO UNIVERSITY   (Japan)

^b TEIKYO UNIVERSITY   (Japan)

^c DAIICHI SANKYO CO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CERAMIDE DERIVATIVE; GALACTOSE; GLOBOTRIAOSYLCERAMIDE; GLUCOSYLCERAMIDE;

ARTICLE; CONTROLLED STUDY; DRUG SYNTHESIS; METHODOLOGY; STEREOCHEMISTRY;

EID: 0030830477     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10365-3     Document Type: Article

References (54)

1. (a) Mootoo, D. R.; Konradsson, P.; Udodong, U.; Fraser-Reid, B. J. Am. Chem. Soc. 1988, 110, 5583.
2. (b) Fraser-Reid, B.; Udodong, U. E.; Wu, Z.; Ottosson, H.; Merritt, J. R.; Rao, C. S.; Roberts, C.; Madsen, R. Synlett 1992, 927.
3. For reviews, see: (a) Toshima, K.; Tatsuta, K. Chem. Rev. 1993, 93, 1503.
4. (b) Boons, G.-J. Tetrahedron 1996, 52, 1095.
5. Roy, R.; Andersson, F. O.; Letellier, M. Tetrahedron Lett. 1992, 33, 6053.
6. (a) Boons, G.-J.; Isles, S. J. Org. Chem. 1996, 61, 4262.
7. (b) Boons, G.-J.; Heskamp, B.; Hout, F. Angew. Chem. Int. Ed. Engl. 1996, 35, 2845.
8. Raghavan, S.; Kahne, D. J. Am. Chem. Soc. 1993, 115, 1580.
9. (a) Yamada, H.; Harada, T.; Miyazaki, H.; Takahashi, T. Tetrahedron Lett. 1994, 35, 3979.
10. (b) Yamada, H.; Harada, T.; Takahashi, T. J. Am. Chem. Soc. 1994, 116, 7919.
11. (a) Ley, S. V.; Priepke, H. W. M. Angew. Chem. Int. Ed. Engl. 1994, 33, 2292.
12. (b) Grice, P.; Ley, S. V.; Pietruszka, J.; Priepke, H. W. M.; Walther, E. P. E. Synlett 1995, 781.
13. Chenault, H. K.; Castro, A. Tetrahedron Lett. 1994, 35, 9145.
14. (a) Kanie, O.; Ito, Y.; Ogawa, T. J. Am. Chem. Soc. 1994, 116, 12073.
15. (b) Kanie, O.; Ito, Y.; Ogawa, T. Tetrahedron Lett. 1996, 37, 4551.
16. (c) Ito, Y.; Kanie, O.; Ogawa, T. Angew. Chem. Int. Ed. Engl. 1996, 35, 2510.
17. (d) Ito, Y.; Ogawa, T. J. Am. Chem. Soc. 1997, 119, 5562.
18. For other chemoselective glycosidation methods, see: (a) Boons, G.-J.; Geurtsen, R.; Holmes, D. Tetrahedron Lett. 1995, 36, 6325.
19. (b) Khiar, N.; Martin-Lomas, M. J. Org. Chem. 1995, 60, 7017.
20. (c) Demchenko, A.; Boons, G.-J. Tetrahedron Lett. 1997, 38, 1629.
21. (d) Boons, G.-J.; Bowers, S.; Coe, D. M. Tetrahedron Lett. 1997, 38, 3773.
22. Hashimoto, S.; Sakamoto, H.; Honda, T.; Ikegami, S. Tetrahedron Lett. 1997, 38, 5181.
23. Naiki, M.; Marcus, D. M. Biochem. Biophys. Res. Commun. 1974, 60, 1105.
24. Wiels, J.; Holmes, E. H.; Cochran, N.; Tursz, T.; Hakomori, S. J. Biol. Chem. 1984, 259, 14783.
25. Kannagi, R.; Levery, S. B.; Ishigami, F.; Hakomori, S.; Shevinsky, L. H.; Knowles, B. B.; Solter, D. J. Biol. Chem. 1983, 258, 8934.
26. Fukuda, M. N.; Bothner, B.; Lloyd, K. O.; Rettig, W. J.; Tiller, P. R.; Dell, A. J. Biol. Chem. 1986, 267, 5145.
27. Kniep, B.; Monner, D. A.; Schwuléra, U.; Mühlradt, P. F. Eur. J. Biochem. 1985, 149, 187.
28. (a) Kint, J. A. Science 1970, 167, 1268.
29. (b) Li, Y.-T.; Li, S.-C. J. Biol. Chem. 1971, 246, 3769.
30. (a) Keusch, G. T.; Jacewicz, M.; Acheson, D. W. K.; Donohue-Rolfe, A.; Kane, A. V.; McCluer, R. H. Infect. Immun. 1995, 63, 1138.
31. (b) Nyholm, P.-G.; Magnusson, G.; Zheng, Z.; Norel, R.; Binnington-Boyd, B.; Lingwood, C. A. Chem. Biol. 1996, 3, 263.
32. Shapiro, D.; Acher, A. J. Chem. Phys. Lipids 1978, 22, 197.
33. Koike, K.; Sugimoto, M.; Sato, S.; Ito, Y.; Nakahara, Y.; Ogawa, T. Carbohydr. Res. 1987, 163, 189.
34. (a) Nicolaou, K. C.; Caulfield, T. J.; Kataoka, H.; Kumazawa, T. J. Am. Chem. Soc. 1988, 110, 7910.
35. (b) Nicolaou, K. C.; Caulfield, T. J.; Kataoka, H. Carbohydr. Res. 1990, 202, 177.
36. Qiu, D.; Schmidt, R. R. Liebigs Ann. Chem. 1992, 217.
37. Sato, S.; Nunomura, S.; Nakano, T.; Ito, Y.; Ogawa, T. Tetrahedron Lett. 1988, 29, 4097.
38. (a) Schmidt, R. R.; Zimmermann, P. Angew. Chem. Int. Ed. Engl. 1986, 25, 725.
39. (b) Schmidt, R. R. In Synthesis in Lipid Chemistry; Tyman, J. H. P., Ed.; Royal Society of Chemistry: Cambridge, 1996; pp 93-118.
40. Hashimoto, S.; Yanagiya, Y.; Honda, T.; Harada, H.; Ikegami, S. Tetrahedron Lett. 1992, 33, 3523.
41. 2, 2,6-lutidine, EtOH, 60 °C, 2 h, 71%.
42. Ogawa, T.; Beppu, K.; Nakabayashi, S. Carbohydr. Res. 1981, 93, C6.
43. 31P NMR) and high resolution mass spectral characteristics.
44. 3) δ 19.66.
45. 35C(O)Cl, NaOAc, THF, 30 min, 91%.
46. Radunz, H.-E.; Devant, R. M.; Eiermann, V. Liebigs Ann. Chem. 1988, 1103.
47. The reduced yield is due to the formation of 22% of α-galactosylceramide (i) and 11% of 4'-deprotected-β-lactosylceramide (ii). matrix presented
48. 3N, MeOH, 1 d; (3) BzCl, pyridine, -40 to 0 °C, 6 h, 63% (2 steps).
49. Fiandor, J.; García-López, M. T.; de las Heras, F. G.; Méndez-Castrillón, P. P. Synthesis 1985, 1121.
50. 4 as an external standard.
51. 2P(O)Cl, HMPA, -20 °C, 2 h, 66%.
52. Fukase, K.; Matsumoto, T.; Ito, N.; Yoshimura, T.; Kotani, S.; Kusumoto, S. Bull. Chem. Soc. Jpn. 1992, 65, 2643.
53. For the use of a lactosyl azidosphingosine segment, see: (a) Nicolaou, K. C.; Caulfield, T. J.; Kataoka, H.; Stylianides, N. A. J. Am. Chem. Soc. 1990, 112, 3693.
54. (b) Liu, K. K.-C.; Danishefsky, S. J. J. Am. Chem. Soc. 1993, 115, 4933.