A stereoselective α-fucosylation reaction using 1-hydroxy 2,3,4-trio- benzyl-L-fucose donor for the practical synthesis of selectin blocker

Bioorganic and Medicinal Chemistry Letters

Volumn 8, Issue 20, 1998, Pages 2845-2848

  Kiyoi, Takao ^a   Kondo, Hirosato ^a  

^a KANEBO LTD   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

1 HYDROXY 2,3,4 TRI O BENZYLFUCOSE; FUCOSE; UNCLASSIFIED DRUG;

ANTIINFLAMMATORY ACTIVITY; ARTICLE; DERIVATIZATION; DRUG SYNTHESIS; FUCOSYLATION; GLYCOSYLATION; LIGAND BINDING; NONHUMAN; REACTION ANALYSIS; STEREOCHEMISTRY;

ANTI-INFLAMMATORY AGENTS, NON-STEROIDAL; CARBOHYDRATE SEQUENCE; DIPEPTIDES; FUCOSE; GLYCOSYLATION; MOLECULAR SEQUENCE DATA; SELECTINS; STEREOISOMERISM;

EID: 0032552843     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(98)00516-2     Document Type: Article

References (18)

1. 1. Sagara, H.; Ra, C.; Okada, T.; Shinohara, S.; Fukuda, T.; Okumura K.; Makino S. Int. Arch. Allergy Immunol. 1996, 111 Suppl 1, 32-36.
2. 2. Grober, J. S.; Bowen, B. L.; Ebling, H.; Athey, B.; Thompson, C. B.; Fox, D. A.; Stoolman, L. M. J. Clin. Invest. 1993, 91, 2609-2619.
3. 3. Lefer, D. J.; Flynn, D. M.; Phillips, M. L.; Ratcliffe, M.; Buda, A. J. Circulation 1994, 90, 2390-2401.
4. 4. Berg, E. L.; Yoshino, T.; Rott, L. S.; Robinson, M. K.; Warnock, R. A.; Kishimoto T. K.; Picker, L. J.; Butcher, E. C. J. Exp. Med. 1991, 174, 1461-1466.
5. 5. Picker, L. J.; Kishimoto, T.K.; Smith, C. W.; Warnock, R. A.; Butcher, E. C. Nature 1991, 349, 796-799.
6. 6. Lin, C.-C.; Shimazaki, M.; Heck, M.-P.; Aoki, S.; Wang, R.; Kimura, T.; Ritzen, H.; Takayama, S.; Wu, S.-H.; Weitz-Shmidt, G.; Wong, C.-H. J. Am. Chem. Soc. 1996, 118, 6826-6840.
7. 7. Bamford, M.J.; Bird, M.; Gore, P. M.; Holmes, D. S.; Priest, R.; Prodger, J. C.; Saez, V. Bioorg. Med. Chem. Lett. 1996, 6, 239-244.
8. 8. Toepfer, A.; Kretzschmar, G. Bioorg. Med. Chem. Lett. 1997, 7, 1311-1316.
9. 9. Toepfer, A.; Kretzschmar, G.; Schuth, S.; Sonnentag, M. Bioorg. Med. Chem. Lett. 1997, 7, 1317-1322.
10. 10. Prodger, J. C.; Bamford, M. J.; Bird, M. I.; Gore, P. M.; Holmes, D. S.; Priest, R.; Saez, V. Bioorg. Med. Chem. 1996, 4, 793-801.
11. 11. Tsukida, T.; Hiramatsu, Y.; Tsujishita, H.; Kiyoi, T.; Yoshida, M.; Kurokawa, K.; Moriyama, H.; Ohmoto, H.; Wada, Y.; Saito, T.; Kondo, H. J. Med. Chem. 1997, 40, 3534-3541.
12. 12. Other Lewis acid mediated glycosylations were reported. For example, (a) Koto, S.; Sato, T.; Morishima, N.; Zen, S. Bull. Chem. Soc. Jpn., 1980, 53, 1761-1762.
13. (b) Koto S.; Yago, K.; Zen, S.; Tomonaga, F.; Shimada, S. Bull. Chem. Soc. Jpn., 1986, 59, 411-414.
14. (c) Uchiro, H.; Miyazaki, K.; Mukaiyama, T. Chem. Lett., 1997, 403-404.
15. (d) Garcia, B. A.; Poole, J. L.; Gin, D. Y.; J. Am. Chem. Soc., 1997, 119, 7597-7598.
16. 13. It was also reported that TMSOTf was a superior reagent for the aryl C-glycosylation reaction. Toshima, K.; Matsuo, G.; Nakata, M. J. Chem. Soc. Chem. Commun., 1994, 997-998.
17. 2 afforded the corresponding product (α/β=60/40).
18. 3CN:0.1%TFA=7:3, flow rate; 1ml/min, column; inertsil ODS-2, HPLC system; Waters model 150, retention time (min); 17.2 for α, 18.2 for β.