Scalable synthesis of L-lduronic acid derivatives via stereocontrolled cyanohydrin reaction for synthesis of heparin-related disaccharides

Organic Letters

Volumn 11, Issue 20, 2009, Pages 4528-4531

  Hansen, Steen Uldall ^a   Baráth, Marek ^a,b   Salameh, Bader A B ^a,c   Pritchard, Robin G ^a   Stimpson, William T ^a   Gardiner, John M ^a   Jayson, Gordon C ^a  

^a UNIVERSITY OF MANCHESTER   (United Kingdom)

^b INSTITUTE OF CHEMISTRY   (Slovakia)

^c HASHEMITE UNIVERSITY   (Jordan)

Author keywords

[No Author keywords available]

Indexed keywords

CYANOHYDRIN; DISACCHARIDE; DRUG DERIVATIVE; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; HEPARIN; IDURONIC ACID; NITRILE;

AIR; ARTICLE; CHEMISTRY; ENZYME SPECIFICITY; STEREOISOMERISM; SYNTHESIS; TEMPERATURE;

AIR; DISACCHARIDES; HEPARIN; IDURONIC ACID; INDICATORS AND REAGENTS; NITRILES; STEREOISOMERISM; SUBSTRATE SPECIFICITY; TEMPERATURE;

EID: 70349929204     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol901723m     Document Type: Article

References (46)

1. (a) Bishop, J.; Schuksz, M: Esko. J. D. Nature 2007, 446, 1030-1037.
2. (b) Turnova, S.: Woods, A.; Couchman, J. R. Int, J. Biochem. Cell Biol. 2000, 32, 269-288.
3. (c) Sasisekharan. R.; Shriver, Z.; Venkataraman, G.; Narayanasami. U. Nat. Rev. Cancer 2002, 2, 521-528.
4. (a) Pellegrini, L. Curr. Opin. Struct. Biol. 2001, 629-634.
5. (b) Hung, K. W.: Kumar, T. K. S.: Kathir. K. M.: Xu, P.: Ni, F.: Ji. H. H. Biochemistry 2005, 44, 15787-15798.
6. (c) Olsen, S. K.; Ibrahimi, O. A.; Raucci, A.: Zhang, F. Proc. Natl. Acad. Sci. 2004, 101, 935-941.
7. Cole. C: Jayson, G. C. Ejpert Opin. Biol. Ther. 2008, 8, 351-362.
8. (a) Rochepeau-Jobron, L: Jacquinet, J.-C. Carbohydr. Res. 1997, 303, 395-406.
9. (b) Hinou, H.: Kuorsawa, H.: Matsuoka, K.; Terunuma, D.; Kuzuhara, H. Trtrahedron Lett. 1999, 40, 1501-1504.
10. (c) Schell, P.: Orgueira, H. A.; Roehrig, S.; Seeberger. P. H. Tgirahedron Lett. 2001. 42, 3811-3814.
11. (d) Orgueira. H. A.; Bartolozzi, A.; Schell, P.; Litjens, R. E. J. N.; Palmacci. E. R.; Seeberger, P. H. Chem.-Eur. J. 2003, 9, 140-169.
12. (e) Ke, W.: Whitfield, D. M.: Gill. M.; Larocque, S.: Yu, S. H. Tetrahedron Lett. 2003, 44, 7767-7770.
13. (f) Ojeda. R.; de Paz, J. L.; MartinLomas, M.; Lassaletta, J. M. Synlett 1999, 1316-1318.
14. (g) acquinet, J-C.; Petitoi, M: Duchaussoy, P.; Lederman. I.; Choay. J.; Torri, G.; Sinay, P. Cyrbohydr. Res. 1984, 130, 221-241.
15. (h) Yu, H. N.; Furukawa, J.-i.; Ikeda, T.; Wong, C. H. Orglett 2004, 6, 723-726. Via C6 bromo:
16. (i) BlancMuesser, M.: Defaye, J.: Horton, D.: Tsai, J.-H. Methods Carbohydr. Chem. 1980, 8. 177-183.
17. (j) Tatai, J.; Osztrovszky, G.: Kajtár-Peredy. M.; Fügedi, P. Carbohydr. Res. 2007, 343. 596-606.
18. (k) Codee, J. D. C.; Stubba, B.; Schiattarella, M.; Overkleeft, H. S.; van Boeckel, C. A.; van Boom, J. H.; van der Marel, G. A. J. Am. Chem. Soc. 2005, 127, 3767-3773.
19. (1) Davis. N. J.; Flitsch, S. L. Tetrahedron Lett. 1993. 34. 1181-1184.
20. Seebach, D. Angew. Chem., Int. Ed. Engl. 1967, 6, 442-443.
21. (a) Lohman, G. J. S.; Hunt, D. K.: Hogermeier, J. A; Seeberger, P. J. Org. Chem. 2003. 68, 7559-7561.
22. (b) Gavard, O.; Hersant. Y. 1.: Alais, J.; Duverger, V.; Dilhas, A.; Baseou, A.; Bonnaffé, D. Eur. J. Org. Chem. 2003, 3603-3620.
23. (c) Lubineau. A.; Gavard, O.; Alais, J.; Bonnaffé, D. Tetrahedron Lett. 2000. 41. 307-311.
24. Polat, T.; Wong, C.-H. J. Am. Chem. Soc. 2007, 127, 12795-12800.
25. (a) Kiliani. H. Ber. 1887. 20, 339.
26. (b) Synder, J. R.; Serianni. A. S. Carbohydr. Res. 1987, 163, 169-188.
27. (c) Synder, J. R.; Serianni, A. S. J. Org. Chem. 1986. 51, 2694-2702.
28. (a) Wolfrom, M. L.: Thomas. G. H. S. Methods Carbohydr. Chem. 1963, 2, 32-34
29. (b) Shafizadeh. F.: Wolfrom, M. L. J. Am. Chem. Soc. 1955, 77, 2568-2569.
30. (c) Hudson, C. S. J. Am. Chem. Soc. 1951. 73. 4498-4499. Idogluco system gave 1:1 ratio under all conditions:
31. (d) Rauter, A.: Figueiredo, J.; Ismael, I.: Pais, M. J. Carbohydr. Chem. 1987. 6, 259-272.
32. (a) Fernández, R.; Martín-Zamora, E.: Pareja. C.; Lassaletta. J. M. J. Org. Chem. 2001, 66, 5201-5207.
33. (b) Fernández, R.; Martín-Zamora, E.: Pareja. C: Lassaletta, J. M. Tetrahedron Lett. 1996, .575787-575790
34. A graphical representation is available in the Supporting Information.
35. 2O: 3, 0.9 mg/mL, and 4, 1.9 mg/ mL.
36. Data deposited with the Cambridge Crystallographic Database and allocated the deposition no.CCDC 736690.
37. H2-H3= 9.8 Hz for 6, while H-4 in 7, for example, shows only J < 5 Hz.
38. Increasing acid concentration in the first step (to effect in situ removal of the 0-4 acetal of 7) was ineffective.
39. Anelli, P.; Brocchetta, M.: Palano, D.; Visigalli. M. Tetrahedron Lett. 1997, 38, 2367-2368.
40. (a) Lohman, G.; Seeberger. P. J. Org. Chem. 2004. 69, 4081-4093.
41. (b) Orgueira, H.: Bartolozzi, A.: Schell, P.: Seeberger, P. Angew. Chem., Int. Ed. 2002, 41, 2128-2131.
42. 1 = CHPh):
43. (b) Ertin Lomas, M.: Flores-Mosquera, M.; Chiara, J. Eur. J. Org. Chem. 2000, 154, 7-1562.
44. 1 = Bn):
45. (c) Lindberg, J.: Ohberg. L.: Garegg, P. J.; Konradsson. P. Tetrahedron Lett. 2002, 58, 1387-1398.
46. The same reactivity trends were evident using corresponding trichloroacetimidate 2-azido gluco donors.