Effective synthesis of negatively charged cyclodextrins. Selective access to phosphate cyclodextrins

Tetrahedron

Volumn 64, Issue 32, 2008, Pages 7587-7593

  López, Óscar ^a   Bols, Mikael ^b  

^a UNIVERSITY OF SEVILLE   (Spain)

^b UNIVERSITY OF COPENHAGEN   (Denmark)

Author keywords

[No Author keywords available]

Indexed keywords

ALPHA CYCLODEXTRIN; BETA CYCLODEXTRIN; CYCLODEXTRIN DERIVATIVE; PHOSPHATE CYCLODEXTRIN;

ANION EXCHANGE CHROMATOGRAPHY; ARTICLE; COMPLEX FORMATION; CRYSTALLIZATION; DEBENZYLATION; DEPROTECTION REACTION; HYDROGENATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PHOSPHORYLATION; PRIORITY JOURNAL; SYNTHESIS;

EID: 45849084231     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2008.05.094     Document Type: Article

References (49)

1. Hedges A.R. Chem. Rev. 98 (1998) 2035-2044
2. Ferrari F., Sorrenti M., Rossi S., Catenacci L., Sandri G., Bonferoni M.C., Caramella C., and Bettinetti G. Pharm. Dev. Technol. 13 (2008) 65-73
3. Liu Z., Sun X., Nakayama-Ratchford N., and Dai H. ACS Nano 1 (2007) 50-56
4. Masar III M.S., Gianneschi N.C., Oliveri C.G., Stern C.L., Nguyen S.T., and Mirkin C.A. J. Am. Chem. Soc. 129 (2007) 10149-10158
5. Carlqvist P., and Maseras F. Chem. Commun. (2007) 748-750
6. Davis A.P., and Wareham R.S. Angew. Chem., Int. Ed. 38 (1999) 2979-2996
7. Shpigun O.A., Ananieva I.A., Budanova N.Yu., and Shapovalova E.N. Russ. Chem. Rev. 72 (2003) 1035-1054
8. Villalonga R., Cao R., and Fragoso A. Chem. Rev. 107 (2007) 3088-3116
9. Engeldinger E., Armspach D., and Matt D. Chem. Rev. 103 (2003) 4147-4173
10. Motherwell W.B., Bingham M.J., and Six Y. Tetrahedron 57 (2001) 4663-4686
11. Breslow R., and Dong S.D. Chem. Rev. 98 (1998) 1997-2011
12. Rousseau C., Ortega-Caballero F., Nordstrøm L.U., Christensen B., Petersen T.E., and Bols M. Chem.-Eur. J. 11 (2005) 5094-5101
13. Helmreich E.J.M., and Klein H.W. Angew. Chem., Int. Ed. Engl. 19 (1980) 441-455
14. Palm D., Blumenauer G., Klein H.W., and Blanc-Muesser M. Biochem. Biophys. Res. Commun. 111 (1983) 530-536
15. Takagi M., Fukui T., and Shimomura S. Proc. Natl. Acad. Sci. U.S.A. 79 (1982) 3716-3719
16. Klein H.W., Im M.J., and Palm D. Eur. J. Biochem. 157 (1986) 107-114
17. Rekharsky M.V., and Inoue Y. J. Am. Chem. Soc. 124 (2002) 813-826
18. Cho A., Ochoa Lara K.L., Yatsimirsky A.K., and Eliseev A.V. Org. Lett. 2 (2000) 1741-1743
19. Eliseev, A. V. PCT WO 2004/050709, A2, 2004.
20. Mlynarz P., Rudzinska E., Berlicki L., and Kafarski P. Curr. Org. Chem. 11 (2007) 1593-1609
21. Cherenok S., Dutasta J.-P., and Kalchenko V. Curr. Org. Chem. 10 (2006) 2307-2331
22. Siegel B., Pinter A., and Breslow R. J. Am. Chem. Soc. 99 (1977) 2309-2312
23. Tarelli E., Lemercinier X., and Wheeler S. Carbohydr. Res. 302 (1997) 27-34
24. Inoue H., Kawashita T., Nakayama H., and Tsuhako M. Carbohydr. Res. 340 (2005) 1766-1772
25. Inoue H., Tone N., Nakayama H., and Tsuhako M. Carbohydr. Res. 338 (2003) 2067-2074
26. Liu Y., Li L., Li X.-Y., Zhang H.-Y., Wada T., and Inoue Y. J. Org. Chem. 68 (2003) 3646-3657
27. Liu Y., Li B., Han B.-H., Li Y.-M., and Chen R.T. J. Chem. Soc., Perkin Trans. 2 (1997) 1275-1278
28. Liu Y., Han B.-H., and Chen Y.-T. J. Phys. Chem. B 106 (2002) 4678-4687
29. Pearce A.J., and Sinaÿ P. Angew. Chem., Int. Ed. 39 (2000) 3610-3612
30. Wang W., Pearce A.J., Zhang Y., and Sinaÿ P. Tetrahedron: Asymmetry 12 (2001) 517-523
31. Guieu S., and Sollogoub M. J. Org. Chem. 73 (2008) 2819-2828
32. Bistri O., Sinaÿ P., Barbero J.J., and Sollogoub M. Chem.-Eur. J. 13 (2007) 9757-9774
33. Lecourt T., Herault A., Pearce A.J., Sollogoub M., and Sinay P. Chem.-Eur. J. 10 (2004) 2960-2971
34. Bjerre J., Nielsen E.H., and Bols M. Eur. J. Org. Chem. (2008) 745-752
35. López López O., Marinescu L., and Bols M. Tetrahedron 63 (2007) 8872-8880
36. Bjerre J., Hauch Fenger T., Marinescu L.G., and Bols M. Eur. J. Org. Chem. (2007) 704-710
37. Marinescu L.G., and Bols M. Angew. Chem., Int. Ed. 45 (2006) 4590-4592
38. Ortega-Caballero F., and Bols M. Can. J. Chem. 84 (2006) 650-658
39. Ortega-Caballero F., Bjerre J., Lausten L.S., and Bols M. J. Org. Chem. 70 (2005) 7217-7226
40. Ortega-Caballero F., Rousseau C., Christensen B., Petersen T.E., and Bols M. J. Am. Chem. Soc. 127 (2005) 3238-3239
41. Marinescu L., Mølbach M., Rousseau C., and Bols M. J. Am. Chem. Soc. 127 (2005) 17578-17579
42. Rousseau C., Christensen B., and Bols M. Eur. J. Org. Chem. (2005) 2734-2739
43. Rousseau C., Christensen B., Petersen T.E., and Bols M. Org. Biomol. Chem. 2 (2004) 3446-3482
44. Yu K.L., and Fraser-Reid B. Tetrahedron Lett. 29 (1988) 979-982
45. Freimund S., Baldes L., Huwig A., and Giffhorn F. Carbohydr. Res. 337 (2002) 1585-1587
46. Lecourt T., Mallet J.-P., and Sinaÿ P. C.R. Chim. 6 (2003) 87-90
47. Clausen M.H., Jørgensen M.R., Thorsen J., and Madsen R. J. Chem. Soc., Perkin Trans. 1 (2001) 543-551
48. McElroy W.D., and Glass B. Phosphorus Metabolism Vol. I (1951), Johns Hopkins University Press, Baltimore, MD
49. Remko M., Van Duijnen P.T., and von der Lieth C.-W. J. Mol. Struct. (Theochem) 814 (2007) 119-125