Synthesis of the non-reducing end trisaccharide of the antithrombin-binding domain of heparin and its bioisosteric sulfonic acid analogues

Tetrahedron

Volumn 68, Issue 36, 2012, Pages 7386-7399

  Lázár, László ^a   Mez, Erika ^a   Herczeg, Mihály ^a   Lipták, András ^a   Antus, Sándor ^a,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 trisaccharides; Sulfonatomethyl analogues

Indexed keywords

1,2 DI O ACETYL 3 O METHYL DEXTRO GLUCOPYRANOSE; 1,2 DI O ACETYL 4,6 O BENZYLIDENE 3 OMETHYL DEXTRO GLUCOPYRANOSE; GLUCURONIC ACID; HEPARIN DERIVATIVE; METHYL (2,3,4 TRI O METHYL ALPHA DEXTRO GLUCOPYRANOSYL)(SODIUM 2,3 DI O METHYL BETA DEXTRO GLUCOPYRANOSYLURONATE) ALPHA DEXTRO GLUCOPYRANOSIDE; METHYL (6 O BENZYL 2,3,4 TRI O METHYL ALPHA DEXTRO GLUCOPYRANOSYL) 2 O ACETYL 3 O METHYL 1 O TRICHLOROACETIMIDOYL DEXTRO GLUCOPYRANOSYLURONATE; METHYL (6 O BENZYL 2,3,4 TRI O METHYL ALPHA DEXTRO GLUCOPYRANOSYL) 2 O ACETYL 3 O METHYL DEXTRO GLUCOPYRANOSYLURONATE; METHYL (6 O BENZYL 2,3,4 TRI O METHYL ALPHA DEXTRO GLUCOPYRANOSYL)(METHYL 3 O METHYL BETA DEXTRO GLUCOPYRANOSYLURONATE) 2,3,6 TRI O BENZYL ALPHA DEXTRO GLUCOPYRANOSIDE; METHYL (SODIUM 4 DEOXY 2,3 DI O METHYL ALPHA LEVO THREO HEX 4 ENOPYRANOSYLURONATE) 2,3,6 TRI O BENZYL ALPHA DEXTRO GLUCOPYRANOSIDE; METHYL 1,2 DI O ACETYL 3 O METHYL ALPHA DEXTRO GLUCOPYRANOSYLURONATE; METHYL 6 O BENZYL 2,3,4 TRI O METHYL ALPHA DEXTRO GLUCOPYRANOSIDE; PHENYL 2,3 DI O ACETYL 4,6 O (2' NAPHTHYL)METHYLENE 1 THIO BETA DEXTRO GLUCOPYRANOSIDE; PHENYL 2,3 DI O ACETYL 4,6 O (4 METHOXYBENZYLIDENE) 1 THIO BETA DEXTRO GLUCOPYRANOSIDE; PHENYL 2,3 DI O ACETYL 6 O (2' NAPHTHYL)METHYL 1 THIO BETA DEXTRO GLUCOPYRANOSIDE; PHENYL 4,6 O (2' NAPHTHYL)METHYLENE 1 THIO BETA DEXTRO GLUCOPYRANOSIDE; PHENYL 4,6 O (4 METHOXYBENZYLIDENE) 1 THIO BETA DEXTRO GLUCOPYRANOSIDE; PHENYL 6 O BENZYL 2,3,4 TRI O METHYL 1 THIO BETA DEXTRO GLUCOPYRANOSIDE; SULFONIC ACID DERIVATIVE; TRISACCHARIDE; UNCLASSIFIED DRUG;

ARTICLE; BLOOD CLOTTING; CHEMICAL REACTION; DRUG STRUCTURE; DRUG SYNTHESIS; PRIORITY JOURNAL;

EID: 84864289536     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2012.06.081     Document Type: Article

References (36)

1. B. Casu Adv. Carbohydr. Chem. Biochem. 43 1985 51 134
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. L. Jin, J.P. Abrahams, R. Skinner, M. Petitou, and R.N. Pike Proc. Natl. Acad. Sci. U.S.A. 94 1997 14683 14688
6. P. Sinaÿ, J.-C. Jacquinet, M. Petitou, P. Duchaussoy, I. Lederman, J. Choay, and G. Torri Carbohydr. Res. 132 1984 C5 C9
7. 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.J. van der Vlugt Carbohydr. Chem. 4 1985 293 321
8. M. Petitou, P. Duchaussoy, I. Lederman, J. Choay, P. Sinaÿ, J.-C. Jacquinet, and G. Torri Carbohydr. Res. 147 1986 221 236
9. C.A.A. van Boeckel, and M. Petitou Angew. Chem., Int. Ed. 43 2004 3118 3133
10. J.M.W. Cheng Clin. Ther. 24 2002 1757 1769
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, G.T. Overklift, and G.T. Overklift Bioorg. Med. Chem. 2 1994 1267 1280
12. A. Gómez-Outes, R. Lecumberri, C. Pozo, and E. Rocha Curr. Vasc. Pharmacol. 7 2009 309 329
13. J. Harenberg Expert Rev. Clin. Pharmacol. 3 2010 9 16
14. C.A.A. van Boeckel, and M. Petitou Angew. Chem., Int. Ed. Engl. 32 1993 1671 1690
15. M. Herczeg, L. Lázár, A. Borbás, A. Lipták, and S. Antus Org. Lett. 11 2009 2619 2622
16. M. Herczeg, L. Lázár, A. Mándi, A. Borbás, I. Komáromi, A. Lipták, and S. Antus Carbohydr. Res. 346 2011 1827 1836
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 1 10 doi:10.1002/chem.201201041
18. L. Lázár, M. Herczeg, A. Fekete, A. Borbás, A. Lipták, and S. Antus Tetrahedron Lett. 51 2010 6711 6714
19. S. Valverde, M. Garcia, A. Gomez, and J.C. Lopez Synlett 2000 22 26
20. S. David, and A. Thieffry C. R. Acad. Sci., Ser. C 279 1974 1045 1047
21. N.J. Davis, and S.L. Flitsch Tetrahedron Lett. 34 1993 1181 1184
22. A.E.J. de Noy, A.C. Besemer, and H. van Bekkum Carbohydr. Res. 269 1995 89 98
23. Y. Zhou, F. Lin, J. Chen, and B. Yu Carbohydr. Res. 341 2006 1619 1629
24. G.J.S. Lohman, D.K. Hunt, J.A. Högermeier, and P.H. Seeberger J. Org. Chem. 68 2003 7559 7561
25. M. Ek, P.J. Garegg, H. Hultberg, and S. Oscarson J. Carbohydr. Chem. 2 1983 331 336
26. T. Das, and M.S. Shashidhar Carbohydr. Res. 297 1997 243 249
27. A. Borbás, M. Csávás, L. Szilágyi, G. Májer, and A.J. Lipták Carbohydr. Chem. 23 2004 133 146
28. L. Lázár, M. Csávás, A. Borbás, Gy Gyémánt, and A. Lipták ARKIVOC vii 2004 196 207
29. G. Zemplén, and E. Pacsu Chem. Ber. 62 1929 1613 1614
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
34. B.K.S. Yeung, D.C. Hill, M. Janicka, and P.A. Petillo Org. Lett. 2 2000 1279 1282
35. L.J. van den Bos, J.D.C. Codée, J.C. van der Toorn, T.J. Boltje, J.H. van Boom, H.S. Overkleeft, and G.A. van der Marel Org. Lett. 6 2004 2165 2168
36. A.B. Smith III, K.J. Hale, L.M. Laakso, K. Chen, and A. Riéra Tetrahedron Lett. 30 1989 6963 6966