Synthesis of four mono-functionalized α-cyclodextrin derivatives for further confirming DIBAL-H-promoted bis-de-O-methylation mechanism

Tetrahedron

Volumn 69, Issue 20, 2013, Pages 4053-4060

  Xiao, Sulong ^a,b   Yang, Ming ^a   Yu, Fei ^a   Zhang, Lihe ^a   Zhou, Demin ^a   Sinaÿ, Pierre ^b   Zhang, Yongmin ^b,c  

^a PEKING UNIVERSITY HEALTH SCIENCE CENTER   (China)

^b Université Pierre et Marie Curie   (France)

^c JIANGHAN UNIVERSITY   (China)

Author keywords

Cyclodextrin; DIBAL H; Mechanism; Synthesis

Indexed keywords

ALPHA CYCLODEXTRIN DERIVATIVE; ALUMINUM DERIVATIVE; DIISOBUTYLALUMINIUM HYDRIDE; FUNCTIONAL GROUP; HYDROXYL GROUP; UNCLASSIFIED DRUG;

ARTICLE; METHYLATION; PRIORITY JOURNAL; SYNTHESIS;

EID: 84876135344     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2013.03.070     Document Type: Article

References (42)

1. H. Dodziuk Cyclodextrins and Their Complexes. Chemistry, Analytical Methods, Applications 2006 Wiley-VCH GmbH & KGaA Weinheim, Germany
2. G. Schmid J.S. zejtli, Comprehensive Supramolecular Chemistry Vol. 3 1996 Pergamon Oxford 615
3. E.B. Marcus Nat. Rev. Drug Deliv. 3 2004 1023 1035
4. A. Hashidzume, and A. Harada Polym. Chem. 2 2011 2146 2154
5. V. Perchyonok, and T. Oberholzer Curr. Org. Chem. 16 2012 2365 2378
6. J. Mosinger, V. Tomankova, I. Nemcova, and J. Zyka Anal. Lett. 34 2001 1979 2004
7. S.F. Lincoln, and D.-T. Pham P.A. Gale, J.W. Steed, Supramolecular Chemistry: From Molecules to Nanomaterials Vol. 3 2012 954 981
8. S. Samakashvili, A. Salgado, G.K.E. Scriba, and B. Chankvetadze Chirality 25 2013 79 88
9. R. Breslow, and S.D. Dong Chem. Rev. 98 1998 1997 2001 and references cited therein
10. S.V. Bhosale, and S.V. Bhosale Mini-Rev. Org. Chem. 4 2007 231 242
11. E.D. Mark, H. Bricout, F. Hapiot, A. Ponchel, S. Tilloy, and E. Monflier Sustainability 1 2009 924 945
12. F. Bellia, D. La-Mendola, C. Pedone, E. Rizzarelli, M. Saviano, and G. Vecchio Chem. Soc. Rev. 38 2009 2756 2781
13. D. French, M.L. Levine, J.H. Pazur, and E. Norberg J. Am. Chem. Soc. 71 1949 353 356
14. A.K. Chatjigakis, C. Donze, and A.W. Coleman Anal. Chem. 64 1992 1632 1634
15. A.R. Bergeron, Y. Machida, and K. Bloch J. Biol. Chem. 250 1975 1223 1230
16. B. Casu, M. Reggiani, and G.R. Sanderson Carbohydr. Res. 76 1979 59 66
17. J. Szejtli Cyclodextrins and Their Inculsion Complexes 1982 Akadémiai Kiadó Budapest
18. T. Chaise, E. Bourgeaux, P. Cardinael, and J.C. Combret Tetrahedron Lett. 45 2004 5853 5856
19. K. Akira, K. Toshiyuki, N. Yohji, and A. Mitsuru J. Org. Chem. 70 2005 1253 1261
20. A. Bsch, and P. Mischnick Biomacromolecules 8 2007 2311 2320
21. A. Favrelle, V. Bonnet, C. Sarazin, and F. Djedaini-Pilard Tetrahedron: Asymmetry 19 2008 2240 2245
22. Y.J. Gan, Y.M. Zhang, C.H. Xiao, C.Y. Zhou, and Y.C. Zhao Carbohydr. Res. 346 2011 389 392
23. H. Kitagishi, K. Kashiwa, and K. Kano Biopolymers 97 2012 11 20
24. J. Szejtli Cyclodextrins and Their Inculsion Complexes 1982 Akadémiai Kiadó Budapest
25. A.R. Khan, P. Forgo, K.J. Stine, and V.T. D'Souza Chem. Rev. 98 1998 1977 1996 and references cited therein
26. T. Chaise, P. Cardinael, S. Tisse, J.C. Combret, and J.P. Bouillon Tetrahedron: Asymmetry 19 2008 348 357
27. G. Di-Fabio, G. Malgieri, C. Isernia, J. D'Onofrio, M. Gaglione, A. Messere, A. Zarrelli, and L. De Napoli Chem. Commun. 2012 3875 3877
28. A.J. Pearce, and P. Sinaÿ Angew. Chem., Int. Ed. 39 2000 3610 3612
29. O. Bistri, P. Sinaÿ, J. Jiménez Barbero, and M. Sollogoub Chem. - Eur. J. 13 2007 9757 9774
30. S. Guieu, and M. Sollogoub J. Org. Chem. 73 2008 2819 2828
31. S. Guieu, and M. Sollogoub Angew. Chem., Int. Ed. 47 2008 7060 7063
32. E. Zaborova, M. Guitet, G. Prencipe, Y. Blériot, M. Ménand, and M. Sollogoub Angew. Chem., Int. Ed. 52 2013 639 644
33. B. Roizel, J.P. Baltaze, and P. Sinaÿ Tetrahedron Lett. 43 2002 2371 2373
34. S.L. Xiao, D.M. Zhou, M. Yang, P. Sinaÿ, M. Sollogoub, and Y.M. Zhang Tetrahedron Lett. 52 2011 5273 5276
35. X. Luo, Y. Chen, J.G. Huber, Y., Zhang, and P. Sinaÿ C. R. Chimie 7 2004 25 28
36. Y. Chen, J.G. Huber, Y. Zhang, and P. Sinaÿ C. R. Chimie 8 2005 27 30
37. S. Xiao, M. Yang, P. Sinaÿ, M. Sollogoub, and Y. Zhang Eur. J. Org. Chem. 2010 1510 1516
38. S.L. Xiao, D.M. Zhou, M. Yang, F. Yu, L.H. Zhang, P. Sinaÿ, and Y.M. Zhang Chin. Chem. Lett. 23 2012 1315 1318
39. C. Remy, S. Ulrike, P.K. Deveshwari, L. Jacques, and L. Raymond Can. J. Chem. 70 1992 1511 1530
40. D.H.R. Barton, and S.W.J. McCombie J. Chem. Soc., Perkin Trans. 1 1975 1574 1585
41. V.T. D'Souza, P. Forgo, and S. Tian Tetrahedron Lett. 37 1996 8309 8312
42. H. Cousin, P. Cardinael, H. Oulyadi, X. Pannecoucke, and J.C. Combret Tetrahedron: Asymmetry 12 2001 81 88