Synthesis of dimeric Lewis X antigenic determinant with azido-type spacer arm by a sequence of regioselective glycosylation steps

Tetrahedron Letters

Volumn 39, Issue 50, 1998, Pages 9143-9146

  Figueroa Pérez, Santiago ^a   Verez Bencomo, Vicente ^a  

^a UNIVERSITY OF HAVANA   (Cuba)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOHYDRATE DERIVATIVE; EPITOPE;

ARTICLE; BLOOD GROUP LEWIS SYSTEM; CANCER DIAGNOSIS; CANCER IMMUNOTHERAPY; CARBOHYDRATE SYNTHESIS; DRUG SYNTHESIS; FUCOSYLATION; GLYCOSYLATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; POLYMERIZATION; REACTION ANALYSIS; SERODIAGNOSIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS;

EID: 0032506572     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)02104-2     Document Type: Article

References (21)

1. 1. a) Kaizu, T.; Levery, S. B.; Nudelman, E.; Stenkamp, R. E.; Hakomori, S. I. J. Biol. Chem. 1986, 261, 11254-8.
2. b) Hakomori, S. I.; Nudelman, E.; Levery, S. B.; Kannagi, R. J. Biol. Chem. 1984, 259, 4672-80.
3. 2. a) Nilsson, M.; Norberg, T. Carbohydr. Res., 1988, 183, 71-82.
4. b) Nilsson, M.; Norberg, T. J. Carbohydr. Chem. 1989, 8, 613-27.
5. c) Kameyama, A.; Ehara, T.; Yamada, Y.; Ishida H.; Kiso, M.; Hasegawa, A. J. Carbohydr. Chem., 1995, 14, 507-23.
6. d) Bommer, R.; Kinzy, W.; Schmidt, R. R. Liebigs Ann. Chem., 1991, 425-33.
7. e) Toepfer, A.; Kinzy, W.; Schmidt, R. R. Liebigs Ann. Chem., 1994, 449-63.
8. 3. a) Nunomura, S.; Iida, M.; Numata, M.; Sugimoto, M.; Ogawa, T. Carbohydr. Res., 1994, 263, C1-C6.
9. b) Ehara, T.; Kameyama, A.; Yamada, Y.; Ishida, H.; Kiso, M.; Hasegawa, A. Carbohydr. Res., 1996, 281, 237-52.
10. c) Zou, W.; Jennings, H. Biorg. Med Chem. Lett., 1997, 7, 647-50.
11. d) Huang, B. G.; Locke, R. D.; Jain, R. K.; Malta, K. L. Biorg. Med. Chem. Lett., 1997, 1157-60.
12. 4. Lay, L.; Manzoni, L.; Schmidt, R. R. Abstracts of Papers, XVIII International Carbohydrate Symposium, Milan, Italy, July 1996, BP166
13. 5. Figueroa Pérez, S.; Verez Bencomo, V. Carbohydr. Res., 1998, submitted
14. 6. Sato, S.; Ito, Y.; Nukada, T.; Nakahara, Y.; Ogawa, T. Carbohydr. Res., 1987, 167, 197-210.
15. 7. Qiu, D.; Ganghi, S. S.; Koganty, R. R. Tetrahedron Lett., 1996, 37, 595-8
16. 8. Greilich, U.; Zimmermann, P.; Jung, K.; Schmidt, R. R. Liebigs Ann. Chem. 1993, 859-64.
17. 3COO).
18. 10. Lemieux, R. U.; Hendricks, K. B.; Stick, R. V.; James, K. J. J. Am. Chem. Soc., 1975, 97, 4056-62.
19. 11. Bose, R.; Shefold, R. Angew. Chem., 1976, 88, 578-79.
20. 12. Paulsen, H.; Helpap, B. Carbohydr. Res., 1991, 216, 289-313.
21. 3), 15.9, 15.6 (C-6c, f).