Practical Total Synthesis of (2S,3S,4R)-1-O-(α-D-Galactopyranosyl)-N-hexacosanoyl-2-amino-1,3,4-octadecanetriol, the Antitumorial and Immunostimulatory α-Galactosylcer-amide, KRN7000

Bioscience, Biotechnology and Biochemistry

Volumn 60, Issue 2, 1996, Pages 288-292

  Morita, Masahiro ^a   Sawa, Eiji ^a   Yamaji, Kazuo ^a   Sakai, Teruyuki ^a   Natori, Takenori ^a   Koezuka, Yasuhiko ^a   Fukushima, Hideaki ^a   Akimoto, Kohji ^a  

^a KIRIN BREWERY CO LTD   (Japan)

Author keywords

galactosylceramide; D lyxose; KRN7000; agelasphins ; Practical total synthesis

Indexed keywords

EID: 0001413882     PISSN: 09168451     EISSN: 13476947     Source Type: Journal    
DOI: 10.1271/bbb.60.288     Document Type: Article

References (23)

1. T. Natori, Y. Koezuka, and T. Higa, Tetrahedron Lett., 34, 5591-5592 (1993).
2. T. Natori, M. Morita, K. Akimoto, and Y. Koezuka, Tetrahedron. 50,2771-2776(1994).
3. K. Akimoto, T. Natori, and M. Morita, Tetrahedron Lett., 34. 5593-5596 (1993).
4. M. Morita, K. Motoki, K. Akimoto, T. Natori, T. Sakai, E. Sawa, K. Yamaji, Y. Koezuka, E. Kobayashi, and H. Fukushima, J. Med. Chem., 38, 2176-2187 (1995).
5. K. Koike, Y. Nakahara, and T. Ogawa, Agric. Biol. Chem 54 663-667 (1990)
6. J. Gigg and R. Gigg, J. Chem. Soc. (C), 1966, 1876-1879.
7. R. Wild and R. R. Schmidt, Liebigs Ann., 1995, 755-764.
8. R. Schaffer. J. Research NBS, 65, 507-512 (1961).
9. T. Bieg and W. Szeja. Synthesis, 1985, 76-77.
10. T. Mukaiyama, Y. Murai, and S. Shoda, Chem. Lett., 1981, 431-432.
11. G. H. Veenman and J. El. van Boom, Tetrahedron Lett., 30, 4283-4286 (1989).
12. N. K. Kochetkov, E. M. Klimov, and N. N. Malysheva, Tetrahedon Lett., 30, 5459-5462 (1989).
13. K. Toshima and K. Tatsuta, Chem. Rev., 93, 1503-1531 (1993).
14. M. Morita, T. Natori, K. Akimoto, T. Ohsawa, H. Fukushima, and Y. Koezuka. Bioorg. Med. Chem. Lett., 5, 699-704 (1995).
15. R. R. Schmidt, Adv. Carbohydr. Chem. Biochem., 50, 21-123 (1994).
16. G. V. Reddy, V. R. Kulkarni, and El. B. Mereyala, Tetrahedron Lett., 30, 4283-4286 (1989).
17. F. Andersson, P. Fügedi, P. J. Garegg, and M. Nashed, Tetrahedron Lett., 27, 3919-3922 (1986).
18. R. U. Lemieux, K. B. Hendriks, R. V. Stick, and K. James, J. Am. Chem. Soc. 97, 4056-4062 (1975).
19. F. J. Kronzer and C. Schuerch. Carbohydr. Res. 33.273-280 (1974).
20. T. Ishikawa and H. G. Fletcher. J. Org. Chem. 34, 563-571 (1969).
21. A. E. Jackson and R. A. W. Johnstone, Synthesis, 1976. 685-687.
22. G. M. Anantharamaiah and K. M. Sivanandaiah. J. Chem. Soc. Perkin Trans. J, 1977, 490-491.
23. S. Hanessian, T. J. Liak, and B. Vanasse, Synthesis, 1981,396-397.