Novel synthesis of 1,2:3,5-di-O-isopropylidene-β-L-idofuranoside and its derivatives at C6

Tetrahedron Letters

Volumn 41, Issue 1, 2000, Pages 77-80

  Hung, Shang Cheng ^a   Puranik, Ramachandra ^a   Chi, Fa Chen ^a,b  

^a INSTITUTE OF CHEMISTRY   (Taiwan)

^b NATIONAL TSING HUA UNIVERSITY   (Taiwan)

Author keywords

Carbohydrates; Hydroboration; Hydrogenation; L idoses

Indexed keywords

GLUCOSE; GLYCOSIDE;

ARTICLE; HYDROGENATION; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0033992226     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)02004-3     Document Type: Article

References (22)

1. (a) Lindahl, U. Pure and Appl. Chem. 1997, 69, 1897.
2. (b) Conrad, H. E. Heparin-Binding Proteins; Academic Press, 1998.
3. Sinaÿ, P.; Jacquinet, J.-C.; Petitou, M.; Duchaussoy, P.; Lederman, I.; Choay, J.; Torri, G. Carbohydr. Res. 1984, 132, C5.
4. (a) van Boeckel, C. A. A.; Petitou, M. Angew. Chem., Int. Ed. Engl. 1993, 32, 1671.
5. (b) Petitou, M.; Hérault, J.-P.; Bernat, A.; Driguez, P.-A.; Duchaussoy, P.; Lormeau, J.-C.; Herbert, J.-M. Nature 1999, 398, 417.
6. Fourmy, D.; Recht, M. I.; Blanchard, S. C.; Puglisi, J. D. Science 1996, 274, 1367.
7. (a) Alper, P. B.; Hendrix, M.; Sears, P.; Wong, C.-H. J. Am. Chem. Soc. 1998, 120, 1965.
8. (b) Greenberg, W. A.; Priestley, E. S.; Sears, P.; Alper, P. B.; Rosenbohm, C.; Hendrix, M.; Hung, S.-C.; Wong, C.-H. J. Am. Chem. Soc. 1999, 121, 6527.
9. Uchio, Y.; Nagasaki, M.; Eguchi, S.; Matsuo, A.; Nakayama, M.; Hayashi, S. Tetrahedron Lett. 1980, 21, 3775.
10. (a) Jacquinet, J.-C.; Petitou, M.; Duchaussoy, P.; Lederman, I.; Choay, J.; Torri, G.; Sinaÿ, P. Carbohydr. Res. 1984, 130, 221.
11. (b) van Boeckel, C. A. A.; Beetz, T.; Vos, J. N.; de Jong, A. J. M.; van Aelst, S. F.; van der Bosch, R. H.; Mertens, J. M. R.; van der Vlugt, F. A. J. Carbohydr. Chem. 1985, 4, 293.
12. Vlahov, I. R.; Linhardt, R. J. Tetrahedron Lett. 1995, 36, 8379.
13. (a) Rochepeau-Jobron, L.; Jacquinet, J.-C. Carbohydr. Res. 1997, 303, 395.
14. (b) Hinou, H.; Kurosawa, H.; Matsuoka, K.; Terunuma, D.; Kuzuhara, H. Tetrahedron Lett. 1999, 40, 1501.
15. Medakovic, D. Carbohydr. Res. 1994, 253, 299.
16. (a) Ko, S. Y.; Lee, A. W. M.; Masamune, S.; Reed III, L. A.; Sharpless, K. B.; Walker, F. J. Tetrahedron 1990, 46, 245.
17. (b) Chida, N.; Yamada, E.; Ogawa, S. J. Carbohydr. Chem. 1988, 7, 555.
18. (c) Paulsen, H. Methods Carbohydr. Chem. 1978, 6, 142.
19. Hodosi, G.; Podányi, B.; Kuszmann, J. Carbohydr. Res. 1992, 230, 327.
20. 5: 245.1388; found: 245.1381.
21. Hughes, N. A.; Munkombwe, N. M. Carbohydr. Res. 1982, 101, 221.
22. The deposited number at the Cambridge Crystallographic Data Centre is CCDC 133558.