Novel syntheses of Idraparinux, the anticoagulant pentasaccharide with indirect selective factor Xa inhibitory activity

Tetrahedron

Volumn 69, Issue 15, 2013, Pages 3149-3158

  Herczeg, Mihály ^a,b   Mez, Erika ^a,c   Lázár, László ^a,b   Fekete, Anikó ^a   Kövér, Katalin E ^b   Antus, Sándor ^b   Borbás, Anikó ^a,c  

^a INSTITUTE OF EXPERIMENTAL MEDICINE   (Hungary)

^b UNIVERSITY OF DEBRECEN   (Hungary)

^c UNIVERSITY OF DEBRECEN   (Hungary)

Author keywords

Blood coagulation; d Glucuronic acid; Glycosylation; Heparinoid pentasaccharide; l Iduronic acid

Indexed keywords

BLOOD CLOTTING FACTOR 10A; BLOOD CLOTTING FACTOR 10A INHIBITOR; GLUCOSE; IDRAPARINUX; IDURONIC ACID; METHYL(2,3,4 TRI O METHYL ALPHA GLUCOPYRANOSYL) (1-4) (SODIUM 2,3 DI O METHYL BETA GLUCOPYRANOSYLURONATE) (1-4) (ALPHA GLUCOPYRANOSYL) (1-4) (SODIUM 2,3 DI O METHYL A IDOPYRANOSYLURONATE) (1-4)ALPHA GLUCOPYRANOSIDE; METHYL(6 O BENZYL 2,3,4 TRI O METHYL ALPHA DEXTRO GLUCOPYRANOSYL) (1-4) (2,3,6 TRI O BENZYL ALPHA GLUCOPYRANOSYL) (1-4) (METHYL 2 O ACETYL 3 O METHYL ALPHA IDOPYRANOSYLURONATE) (1-4) 2,3,6 TRI O BENZYL ALPHA GLUCOPYRANOSIDE; METHYL(6 O BENZYL 2,3,4 TRI O METHYL ALPHA GLUCOPYRANOSYL) (1-4) (METHYL 2,3 DI O METHYL BETA GLUCOPYRANOSYLURONATE) (1-4) (METHYL 2,3 DI O METHYL A IDOPYRANOSYLURONATE) (1-4) 2,3,6 TRI O BENZYL ALPHA GLUCOPYRANOSIDE; METHYL[2,3,6 TRI O BENZYL 4 O(4 METHOXYBENZYL)ALPHA,BETA GLUCOPYRANOSYL] (1-4) 1,2 DI O ACETYL 3 O METHYL BETA IDOPYRANOSYLURONATE; METHYL[2,3,6 TRI O BENZYL 4 O(4 METHOXYBENZYL)ALPHA,BETA GLUCOPYRANOSYL] (1-4) 2 O ACETYL 3 O METHYL 1 O TRI CHLOROACETIMIDOYL ALPHA,BETA IDOPYRANOSYLURONATE; METHYL[2,3,6 TRI O BENZYL 4 O(4 METHOXYBENZYL)ALPHA,BETA GLUCOPYRANOSYL] (1-4) 2 O ACETYL 3 O METHYL ALPHA,BETA IDOPYRANOSURONATE; NONA SODIUM[METHYL(2,3,4 TRI O METHYL 6 O SULFONATO ALPHA GLUCOPYRANOSYL) (1-4) (2,3 DI O METHYL BETA GLUCOPYRANOSYLURONATE) (1-4) 2,3,6 TRI O SULFONATO ALPHA GLUCOPYRANOSIDE]; PENTASACCHARIDE; PHENYL 2,3 DI O BENZYL 4 O(4 METHOXYBENZYL) 1 THIO BETA GLUCOPYRANOSIDE; PHENYL 2,3,6, TRI O BENZYL 4 O(4 METHOXYBENZYL) 1 THIO BETA GLUCOPYRANOSIDE; TRISACCHARIDE; UNCLASSIFIED DRUG;

ANTICOAGULATION; ARTICLE; DRUG SYNTHESIS; GLYCOSYLATION; OXIDATION; PRIORITY JOURNAL;

EID: 84875215613     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2013.02.076     Document Type: Article

References (33)

1. J.W. Eikelboom, and J.I. Witz Circulation 121 2010 1523 1532
2. R.D. Rosenberg, and P.S. Damus J. Biol. Chem. 248 1973 6490 6505
3. J. Choay, J.-C. Lormeau, M. Petitou, P. Sinaÿ, and J. Fareed Ann. N.Y. Acad. Sci. 370 1981 644 649
4. L. Thunberg, G. Backström, and U. Lindahl Carbohydr. Res. 100 1982 393 410
5. Y.S. Kim, K.B. Lee, and R.J. Linhardt Thromb. Res. 51 1988 97 104
6. M. Petitou, V. Nancy-Portebois, G. Dubreucq, V. Motte, D. Meuleman, M. de Kort, C.A.A. van Boeckel, G.M.T. Vogel, and J.A.J. Wisse Thromb. Haemostasis 102 2009 808 810
7. C.A.A. van Boeckel, and M. Petitou Angew. Chem., Int. Ed. Engl. 32 1993 1671 1690
8. C.A.A. van Boeckel, and M. Petitou Angew. Chem., Int. Ed. 43 2004 3118 3133
9. P. Sinaÿ, J.-C. Jacquinet, M. Petitou, P. Duchaussoy, I. Lederman, J. Choay, and G. Torri Carbohydr. Res. 132 1984 C5 C9
10. C.A.A. van Boeckel, T. Beetz, J.N. Vos, A.J.M. de Jong, S.F. van Aelst, R.H. van den Bosch, J.M.R. Mertens, and F.A. van der Vlugt J. Carbohydr. Chem. 4 1985 293 321
11. P. Westerduin, C.A.A. van Boeckel, J.E.M. Basten, M.A. Broekhoven, H. Lucas, A. Rood, H. van der Heiden, R.G.M. van Amsterdam, T.G. van Dinther, D.G. Meuleman, A. Visser, G.M.T. Vogel, J.B.L. Damm, and G.T. Overklift Bioorg. Med. Chem. 2 1994 1267 1280
12. J. Harenberg Thromb. Haemostasis 102 2009 811 815
13. M. Herczeg, L. Lázár, A. Borbás, A. Lipták, and S. Antus Org. Lett. 11 2009 2619 2622
14. L. Lázár, M. Herczeg, A. Fekete, A. Borbás, A. Lipták, and S. Antus Tetrahedron Lett. 51 2010 6711 6714
15. M. Herczeg, L. Lázár, A. Mándi, A. Borbás, I. Komáromi, A. Lipták, and S. Antus Carbohydr. Res. 346 2011 1827 1836
16. L. Lázár, E. Mez, M. Herczeg, A. Lipták, S. Antus, and A. Borbás Tetrahedron 68 2012 7386 7399
17. M. Herczeg, L. Lázár, Zs. Bereczky, K.E. Kövér, I. Timári, J. Kappelmayer, A. Lipták, S. Antus, and A. Borbás Chem. - Eur. J. 18 2012 10643 10652
18. Ch. Chen, and B. Yu Bioorg. Med. Chem. Lett. 19 2009 3875 3879
19. F.P. Boulineau, and A. Wei J. Org. Chem. 69 2006 3391 3399
20. J.M. Hernandez-Torres, J. Achkar, and A. Wei J. Org. Chem. 69 2004 7206 7211
21. A. Lipták, I. Jodál, and P. Nánási Carbohydr. Res. 44 1975 1 11
22. A. Borbás, Z.B. Szabó, L. Szilágyi, A. Bényei, and A. Lipták Tetrahedron 58 2002 5723 5732
23. Zs. Jakab, A. Mándi, A. Borbás, A. Bényei, I. Komáromi, L. Lázár, S. Antus, and Lipták Carbohydr. Res. 344 2009 2444 2453
24. J.D.C. Codée, G.A. van der Marel, C.A.A. van Boeckel, and J.H. van Boom Eur. J. Org. Chem. 2002 3954 3965
25. H.A. Orgueira, A. Bartolozzi, P. Schell, R.E.J.N. Litjens, E.R. Palmacci, and P.H. Seeberger Chem. - Eur. J. 9 2003 140 169
26. J.D.C. Codée, L.J. van den den Bos, R.E.J.N. Litjens, H.S. Overkleeft, J.H. van Boom, and G.A. van der Marel Org. Lett. 5 2003 1947 1950
27. G.J.S. Lohman, D.K. Hunt, J.A. Högermeier, and P.H. Seeberger J. Org. Chem. 68 2003 7559 7561
28. M. Ek, P.J. Garegg, H. Hultberg, and S. Oscarson J. Carbohydr. Chem. 2 1983 305 311
29. T. Das, and M.S. Shashidhar Carbohydr. Res. 297 1997 243 249
30. J. Xia, S.A. Abbas, R.D. Locke, C.F. Piskorz, J.L. Alderfer, and K.L. Matta Tetrahedron Lett. 41 2000 169 173
31. J.A. Wright, J. Yu, and J.B. Spencer Tetrahedron Lett. 42 2001 4033 4036
32. A. De Mico, R. Margarita, R. Parlanti, A. Vescovi, and G.J. Piancatelli J. Org. Chem. 62 1997 6974 6977
33. J.B. Epp, and T.S. Widlanski J. Org. Chem. 64 1999 293 295