New accesses to L-iduronyl synthons

Tetrahedron Letters

Volumn 41, Issue 3, 2000, Pages 307-311

  Lubineau, A ^a   Gavard, O ^a   Alais, J ^a   Bonnaffe D ^a  

^a CNRS   (France)

Author keywords

Glycosaminoglycans; Heparin; L idose; L iduronic acid; Organometallic; Oxidation

Indexed keywords

ALDEHYDE DERIVATIVE; GLYCOSAMINOGLYCAN; HEPARIN; IDURONIC ACID; ORGANOMETALLIC COMPOUND; URONIC ACID;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; OXIDATION; REACTION ANALYSIS; SYNTHESIS;

EID: 0034650428     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)02080-8     Document Type: Article

References (31)

1. (a) Van Boeckel, C. A. A.; Petitou, M. Angew. Chem., Int. Ed. Engl. 1993, 32, 1671-1818.
2. (b) Ornitz, D. M.; Herr, A. B.; Nilsson, M.; Westman, J.; Svahn, C. M.; Waksman, G. Science 1995, 268, 432-436.
3. © Petitou, M.; Hérault, J. P.; Bernat, A.; Driguez, P. A.; Duchaussoy, P.; Lormeau, J. C.; Herbert, J. M. Nature 1999, 398, 417-422.
4. (d) Lortat-Jacob, H.; Turnbull, J. E.; Grimaud, J. A. Biochem. J. 1995, 310, 497-505.
5. (a) Macher, I.; Dax, K.; Wanek, E.; Weidmann, H. Carbohydr. Res. 1980, 80, 45-51.
6. (b) Jacquinet, J. C.; Petitou, M.; Duchaussoy, P.; Lederman, I.; Choay, J.; Torri, G.; Sinaÿ, P. Carbohydr. Res. 1984, 130, 183-193.
7. © Baggett, N.; Samra, A. K. Carbohydr. Res. 1984, 127, 149-153.
8. (d) Medakovic, D. Carbohydr. Res. 1994, 253, 299-300.
9. (e) Dromowicz, M.; Köll, P. Carbohydr. Res. 1998, 308, 169-171.
10. (f) Hinou, H.; Kurosawa, H.; Matsuoka, K.; Terunuma, D.; Kuzuhara, H. Tetrahedron Lett. 1999, 40, 1511-1504, and references cited therein.
11. (g) Adinolfi, M.; Barone, G.; De Lorenzo, F.; Iadonisi, A. Synlett 1999, 336-338.
12. (f) Ojeda, R.; De Paz, J. L.; Martin-Lomas, M.; Lassaletta, J. M. Synlett 1999, 1316-1318.
13. (a) Horton, D.; Swanson, F. O. Carbohydr. Res. 1970, 14, 159-171.
14. (b) Horton, D.; Tsai, J.H. Carbohydr. Res. 1977, 58, 89-108.
15. Danishefsky, S. J.; DeNinno, M. P.; Philips, G. B.; Zelle, R. E.; Lartey, P. A. Tetrahedron 1986, 42, 2809-2819.
16. Von dem Bussche-Hünnefeld, J. L.; Seebach, D. Tetrahedron 1992, 48, 5719-5730.
17. Seyferth, D.; Weiner, M. A. J. Am. Chem. Soc. 1961, 83, 3583-3585.
18. 3 oxygen instead of the endocyclic oxygen.
19. Imamoto, T.; Kusumoto, T.; Tawarayama, Y.; Sugiura, Y.; Mita, T.; Hatanaka, Y.; Yokoyama, M. J. Org. Chem. 1984, 49, 3904-3912.
20. Ramanathan, V.; Levine, R. J. Org. Chem. 1962, 27, 1216-1219.
21. Seebach, D. Angew. Chem., Int. Ed. Engl. 1967, 6, 442-443.
22. 3CLi may also take its source in the presence of the sulfur atoms which may promote the formation of a complex between the two reactants.
23. CH arom).
24. 13C NMR.
25. Woessner, W. D. Chem. Lett. 1976, 43-46.
26. This combination has been used to reveal aldehyde from thioacetals (Mukayama, T.; Narasaka, K.; Furusato, M. J. Am. Chem. Soc. 1972, 94, 8641-8642) and thiazole (Dondoni, A.; Marra, A.; Perrone, D. J. Org. Chem. 1993, 58, 275-277).
27. This combination has been used to reveal aldehyde from thioacetals (Mukayama, T.; Narasaka, K.; Furusato, M. J. Am. Chem. Soc. 1972, 94, 8641-8642) and thiazole (Dondoni, A.; Marra, A.; Perrone, D. J. Org. Chem. 1993, 58, 275-277).
28. 2 needed to dissolve the starting material.
29. Lubineau, A.; Bonnaffé, D. Eur. J. Org. Chem. 1999, 2, 2523-2532.
30. This aldehyde oxidation with m-CPBA is rather general and other examples including oxidation of acid-labile compounds in buffered conditions will be published in due course.
31. Lubineau, A.; Escher, S.; Alais, J.; Bonnaffé, D. Tetrahedron Lett. 1997, 38, 4087-4090.