Reciprocal donor-acceptor selectivity: The influence of the donor O-2 substituent in the regioselective mannosylation of myo-inositol orthopentanoate

European Journal of Organic Chemistry

Volumn , Issue 3, 2009, Pages 403-411

  Uriel, Clara ^a   Gómez, Ana M ^a   López, J Cristóbal ^a   Fraser Reid, Bert ^b  

^a INSTITUTO DE QUÍMICA ORGÁNICA GENERAL   (Spain)

^b Natural Products and Glycotechnology Research Institute Inc NPG   (United States)

Author keywords

Carbohydrates; Donor acceptor systems; Glycosides; Glycosylation; myo inositol; n Pentenyl orthoester; Regioselectivity; Thioglycoside

Indexed keywords

EID: 58649120073     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200800991     Document Type: Article

References (35)

1. a) H. Paulsen, Angew. Chem. Int. Ed. Engl. 1982, 21, 155-173;
2. b) R. R. Schmidt, Angew. Chem. Int. Ed. Engl. 1986, 25, 212-235;
3. c) K. Toshima, K. Tatsuta, Chem. Rev. 1993, 93, 1503-1531.
4. B. M. Trost, Science 1983, 219, 245-250.
5. N. M. Spijker, C. A. A. van Boeckel, Angew. Chem. Int. Ed. Engl. 1991, 30, 181-183.
6. a) J. M. Sugihara, Adv. Carbohydr. Chem. Biochem. 1953, 8, 1-44;
7. b) A. H. Haines, Adv. Carbohydr. Chem. Biochem. 1976, 33, 11-109.
8. a) B. Fraser-Reid, J. C. López, K. V. Radhakrishnan, M. V. Nandakumar, A. M. Gómez, C. Uriel, Chem. Commun. 2002, 2104-2105;
9. b) B. Fraser-Reid, J. C. López, K. V. Radhakrishnan, M. Mach, A. M. Gómez, C. Uriel, J. Am. Chem. Soc. 2002, 124, 3198-3199;
10. c) C. Uriel, A. M. Gómez, J. C. López, B. Fraser-Reid, Synlett 2003, 2203-2207;
11. d) B. Fraser-Reid, J. C. López, A. M. Gómez, C. Uriel, Eur. J. Org. Chem. 2004, 1387-1395.
12. C. Uriel, A. M. Gómez, J. C. López, B. Fraser-Reid, J. Carbohydr. Chem. 2005, 24, 665-675.
13. C. Uriel, A. Agocs, A. M. Gómez, J. C. López, B. Fraser-Reid, Org. Lett. 2005, 7, 4899-4902.
14. a) B. Fraser-Reid, J. C. López, K. V. Radhakrishnan, M. Mach, U. Schlueter, A. M. Gómez, C. Uriel, Can. J. Chem. 2002, 80, 1075-1087;
15. b) B. Fraser-Reid, G. Anilkumar, L. G. Nair, K. V. Radhakrishnan, J. C. López, A. M. Gómez, C. Uriel, Aust. J. Chem. 2002, 55, 123-130.
16. H. W. Lee, Y. Kishi, J. Org. Chem. 1985, 50, 4402-4404.
17. K. M. Sureshan, M. S. Shashidar, T. Praveen, T. Das, Chem. Rev. 2003, 103, 4477-4504.
18. B. Bernet, A. Vasella, Helv. Chim. Acta 2000, 83, 995-1021.
19. S. Ozaki, V. Koga, L. Ling, Y. Watanabe, Y. Kimura, M. Hirata, Bull. Chem. Soc. Jpn. 1994, 67, 1058-1063.
20. M. Flores-Mosquera, M. Martin-Lomas, J. L. Chiara, Tetrahedron Lett. 1998, 39, 5085-5088.
21. D. C. Billington, R. Baker, J. J. Kulagowski, I. M. Mawer, J. P. Vacca, S. J. de Solms, J. R. Huff, J. Chem. Soc. Perkin Trans. 1 1989, 1423-1429.
22. a) A. Zapata, B. Bernet, A. Vasella, Helv. Chim. Acta 1996, 79, 1169-1191;
23. b) K. Briner, B. Bernet, J.-L. Maloisel, A. Vasella, Helv. Chim. Acta 1994, 77, 1969-1984;
24. c) P. Uhlmann, A. Vasella, Helv. Chim. Acta 1994, 77, 1175-1192;
25. d) E. Bozo, A. Vasella, Helv. Chim. Acta 1994, 77, 745-753;
26. e) P. R. Muddasani, B. Bernet, A. Vasella, Helv. Chim. Acta 1994, 77, 334-350;
27. f) P. R. Muddasani, E. Bozo, B. Bernet, A. Vasella, Helv. Chim. Acta 1994, 77, 257-290.
28. P. Uhlmann, A. Vasella, Helv. Chim. Acta 1992, 75, 1979-1994.
29. M. A. Biamonte, A. Vasella, Helv. Chim. Acta 1998, 81, 688-694.
30. J. C. López, A. M. Gómez, C. Uriel, B. Fraser-Reid, Tetrahedron Lett. 2003, 44, 1417-1420.
31. a) M. Mach, U. Schlueter, F. Mathew, B. Fraser-Reid, K. C. Hazen, Tetrahedron 2002, 58, 7345-7354;
32. b) K. N. Jayaprakash, S. R. Chaudhuri, C. V. S. R. Murty, B. Fraser-Reid, J. Org. Chem. 2007, 72, 5534-5545;
33. c) B. Fraser-Reid, J. C. López, Orthoesters and Related derivatives (Ed.: A. V. Demchenko), Handbook of Chemical Glycosylation, Wiley-VCH, Weinheim, ch. 5.1. 2008.
34. B. Fraser-Reid, U. E. Udodong, Z. Wu, H. Ottosson, J. R. Merritt, C. S. Rao, C. Roberts, R. Madsen, Synlett 1992, 927-942.
35. Z. J. Li, P. L. Liu, Z. J. Li, D. X. Qiu, M. S. Cai, Synth. Commun. 1990; 20, 2169-2175.