Pentaerythritol as the core of multivalent glycolipids: Synthesis of a glycolipid with three SO3Lea ligands

Organic Letters

Volumn 7, Issue 17, 2005, Pages 3753-3756

  Xue, Jie ^a,c   Zhu, Junmin ^b   Marchant, Roger E ^b   Guo, Zhongwu ^a,c  

^a CASE WESTERN RESERVE UNIVERSITY   (United States)

^b Case Western Reserve University   (United States)

^c WAYNE STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

GLYCOLIPID; LIGAND; PENTAERYTHRITOL; PROPANEDIOL DERIVATIVE;

ARTICLE; BLOOD GROUP LEWIS SYSTEM; CARBOHYDRATE ANALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; SYNTHESIS;

CARBOHYDRATE SEQUENCE; GLYCOLIPIDS; LEWIS BLOOD-GROUP SYSTEM; LIGANDS; MOLECULAR STRUCTURE; PROPYLENE GLYCOLS;

EID: 24044484218     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0514202     Document Type: Article

References (23)

1. Lee, Y. C.; Lee, R. T. Acc. Chem. Res. 1995, 28, 321-327.
2. Lee, R. T.; Lee, Y. C. Glycoconjugate J. 2000, 17, 543-551.
3. Lundquist, J. J.; Toone, E. J. Chem. Rev. 2002, 102, 555-578.
4. Roy, R. Trends Glycosci. Glycotechnol. 2003, 15, 291-310.
5. Kawakami, S.; Yamashita, F.; Nishida, K.; Nakamura, J.; Hashida, M. Crit. Rev. Ther. Drug Carrier Syst. 2002, 19, 171-190.
6. Sihorkar, V.; Vyas, S. P. J. Pharm. Pharm. Sci. 2001, 4, 138-158.
7. Jones, M. N. Adv. Drug Delivery Rev. 1994, 13, 215-249.
8. Spevack, W.; Foxall, C.; Charych, D. H.; Dasgupa, F.; Nagy, J. O. J. Med. Chem. 1996, 39, 1018-1020.
9. DeFrees, S. A.; Philips, L.; Guo, L.; Zalipsky, S. J. Am. Chem. Soc. 1996, 118, 6101-6102.
10. Sun, X.; Kanie, Y.; Guo, C.; Kanie, O.; Suzuki, Y.; Wong, C.-H. Eur. J. Org. Chem. 2000, 14, 2643-2653.
11. Bruehl, R. E.; Dasgupta, F.; Katsumoto, T. R.; Tan, J. H.; Bertozzi, C. R.; Spevak, W.; Ahn, D. J.; Rosen, S. D.; Nagy, J. O. Biochemistry 2001, 40, 5964-5974.
12. Yan, F.; Xue, J.; Zhu, J.; Marchant, R. E.; Guo, Z. Bioconjugate Chem. 2005, 16, 90-96.
13. McEver, R. P. Thromb. Haemostasis 1991, 65, 223-228.
14. Bertozzi, C. R. Chem. Biol. 1995, 2, 703-708 and references therein.
15. Somers, W. S.; Tang, J.; Shaw, G. D.; Camphausen, R. T. Cell 2000, 103, 467-479.
16. Zhu, J.; Yan, F.; Guo, Z.; Marchant, R. E. J. Coll. Interface Sci. 2005, in press.
17. Schmidt, M.; Dobner, B.; Nuhn, P. Synlett 2000, 1157-1159.
18. Schmidt, M.; Dobner, B.; Nuhn, P. S. Eur. J. Org. Chem. 2002, 67, 669-674.
19. Kornilov, A. V.; Sherman, A. A.; Kononov, L. O.; Shashkov, A. S.; Nifant'ev, N. E. Carbohydr. Res. 2000, 329, 717-730.
20. Yudina, O. N.; Sherman, A. A.; Nifantiev, N. E. Carbohydr. Res. 2001, 332, 363-371.
21. Norburg, T. In Modern Methods in Carhohydrate Synthesis; Khan, S. H., O'Nell, R. A., Khan, S. H., O'Nell, R. A., Eds.; Harwood Academic Publishers: Amsterdam, The Netherlands, 1996; pp 82-106.
22. Lemieux, R. U.; Hendriks, K. B.; Stick, R. V.; James, K. J. Am. Chem. Soc. 1975, 97, 4056-4062.
23. Sato, S.; Mori, M.; Ito, Y.; Ogawa, T. Carbohydr. Res. 1986, 155, C6.