Stereoselective synthesis of carba- and C-glycosyl analogs of fucopyranosides

European Journal of Organic Chemistry

Volumn , Issue 7, 2000, Pages 1285-1296

  Carpintero, Mercedes ^a   Jaramillo, Carlos ^a,b   Fernández Mayoralas, Alfonso ^a  

^a INSTITUTO DE QUÍMICA ORGÁNICA GENERAL   (Spain)

^b ELI LILLY AND COMPANY   (Spain)

Author keywords

Carbocycles; Carbohydrates

Indexed keywords

FUCOPYRANOSIDE DERIVATIVE; PYRANOSIDE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; GLYCOSYLATION; HYDROGENATION; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0034010412     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/1099-0690(200004)2000:7<1285::AID-EJOC1285>3.0.CO;2-Z     Document Type: Article

References (56)

1. [1a] J. H. Musser Ann. Rep. Med. Chem. 1992, 27, 301-310.
2. [1b] Z. J. Witczak in Carbohydrates in Drug Design (Eds.: Z. J. Witczak, K. A. Nieforth), Marcel Dekker Inc., New York, 1997; pp 1-37.
3. [2a] A. Varki, Glycobiology 1993, 3, 97-130.
4. [2b] R. A. Dwek, Chem. Rev. 1996, 96, 683-720.
5. Carbohydrate Mimics. Concepts and Methods (Ed.: Y. Chapleur), Wiley-VCH, Weinheim, 1998.
6. P. Sears, C.-H. Wong, Chem. Commun. 1998, 1161-1170.
7. [5a] B. Aguilera, A. Fernández-Mayoralas, Chem. Commun. 1996, 127-128.
8. [5b] B. Aguilera, A. Fernández-Mayoralas, J. Org. Chem. 1998, 63, 2719-2723.
9. [6a] For a preliminary account of this work, see: M. Carpintero, A. Fernández-Mayoralas, C. Jaramillo, J. Org. Chem. 1997, 62, 1916-1917.
10. [6b] C. Jaramillo, G. Corrales, A. Fernández-Mayoralas, Tetrahedron Lett. 1998, 39, 7783-7786.
11. x mimics, see: E. E. Simanek, G. J. McGarvey, J. A. Jablonowski, C.-H. Wong, Chem. Rev. 1998, 98, 833-862.
12. [8a] H. Redlich, W. Sudau, A. K. Szardenings, R. Vollerthun, Carbohydr. Res. 1992, 226, 57-78.
13. [8b] S. Cai, M. R. Stroud, S. Hakomori, T. Toyokuni, J. Org. Chem. 1992, 57, 6693-6696.
14. [8c] R. Verduyn, S. H. van Leeuwen, G. A. van der Marel, J. H. van Boom, Recl. Trav. Chim. Pays-Bas 1996, 115, 67-71.
15. [8d] H. A. J. Carless, S. S. Malik, J. Chem. Soc., Chem. Commun. 1995, 2447-2448.
16. [8e] C. H. Tran, D. H. G. Crout, Tetrahedron: Asymmetry 1996, 7, 2403-2406.
17. [8f] R. Angelaud, Y. Landais, Tetrahedron Lett. 1997, 38, 8841-8844.
18. D. E. Levy, C. Tang, The Chemiatry of C-Glycosides, Pergamon, Exeter, 1995.
19. For samarium diiodide promoted pinacol coupling of related carbohydrate derivatives, see: [10a] J. L. Chiara, W. Cabri, S. Hanessian, Tetrahedron Lett. 1991, 32, 1125-1128.
20. [10b] J. Uenishi, S. Masuda, S. Wakabayashi, Tetrahedron Lett. 1991, 32, 5097-5100.
21. [10c] J. L. Chiara, M. Martin-Lomas, Tetrahedron Lett. 1994, 35, 2969-2972.
22. [10d] J. P. Guidot, T. Le Gall, C. Mioskowski, Tetrahedron Lett. 1994, 35, 6671-6672.
23. [10e] J. L. Chiara, N. Valle, Tetrahedron: Asymmetry 1995, 6, 1895-1898.
24. [10f] T. Sawada, R. Shirai, S. Iwasaki, Tetrahedron Lett. 1996, 37, 885-886.
25. E. J. Corey, R. A. E. Winter, J. Am. Chem. Soc. 1963, 85, 2677-2678.
26. For selective lipase-catalyzed acylations controlled by solvent, see: [12a] R. López, E. Montero, F. Sánchez, J. Cañada, A. Fernãndez Mayoralas, J. Org. Chem. 1994, 59, 7027-7032.
27. [12b] D. A. MacManus, E. N. Vulfson, Enzyme Microb. Technol. 1997, 20, 225-228.
28. [13a] G. Stork, T. Y. Chan, G. A. Breault, J. Am. Chem. Soc. 1992, 114, 7578-7579.
29. [13b] L. Pingli, M. Vandewalle, Tetrahedron 1994, 50, 7061-7074.
30. [13c] L. Fensterbank, A-L. Dhimane, S. Wu, E. Lâcote, S. Bogen, M. Malacria, Tetrahedron 1996, 52, 11405-11420.
31. 3) spectrum.
32. Elimination of a cyclic sulfate derived from dimethyl L-tartrate to give a vinyl sulfate salt was reported previously: K. S. Kim, G. W. Lee, I. H. Cho, Y. H. Joo, Bull. Korean Chem. Soc. 1993, 14, 660-661.
33. 1H NMR spectra of 17 and 26 (see Scheme 6).
34. W. Wittman, H. Kessler, Angew. Chem. 1993, 105, 1138-1140; Angew. Chem. Int. Ed. Engl. 1993, 32, 1091-1093.
35. W. Wittman, H. Kessler, Angew. Chem. 1993, 105, 1138-1140; Angew. Chem. Int. Ed. Engl. 1993, 32, 1091-1093.
36. [18a] T. Skrydstrup, O. Jarreton, D. Mazéas, D. Urban, J.-M. Beau, Chem. Eur. J. 1998, 4, 655-671.
37. [18b] D. Mazéas, T. Skrydstrup, J.-M. Beau, Angew. Chem. 1995, 107, 990-993; Angew. Chem. Int. Ed. Engl. 1995, 34, 909-912.
38. [18b] D. Mazéas, T. Skrydstrup, J.-M. Beau, Angew. Chem. 1995, 107, 990-993; Angew. Chem. Int. Ed. Engl. 1995, 34, 909-912.
39. [18c] P. de Pouilly, A. Chénedé, J.-M. Mallet, P. Sinaÿ, Bull. Soc. Chim. Fr. 1993, 130, 256-265.
40. S.-C. Hung, C.-H. Wong, Angew. Chem. 1996, 108, 2829-2832; Angew. Chem. Int. Ed. Engl. 1996, 35, 2671-2674.
41. S.-C. Hung, C.-H. Wong, Angew. Chem. 1996, 108, 2829-2832; Angew. Chem. Int. Ed. Engl. 1996, 35, 2671-2674.
42. S.-C. Hung, C.-H. Wong, Tetrahedron Lett. 1996, 37, 4903-4906.
43. [21a] O. Frey, M. Hoffmann, V. Wittman, H. Kessler, P. Uhlmann, A. Vasella, Helv. Chim. Acta 1994, 77, 2060-2069.
44. [21b] P. Lesimple, J.-M. Beau, Bioorg. Med. Chem. 1994, 2, 1319-1330.
45. A. Furstner, Liebigs Ann. Chem. 1993, 1211-1217.
46. K. C. Nicolaou, R. E. Dolle, D. P. Papahatjis, J. L. Randall, J. Am. Chem. Soc. 1984, 106, 4189-4192.
47. P. Smid, G. A. van der Marel, F. M. Rombouts, J. H. van Boom, J. Carbohydr. Chem. 1991, 10, 833-849.
48. T. Uchiyama, O. Hindsgaul, Synlett 1996, 499-501.
49. J.-M. Beau, P. Sinaÿ, Tetrahedron Lett. 1985, 26, 6185-6188; 6189-6192.
50. 1,2 = 3.0 Hz), but no signals were observed for an aglycon moiety. The mass spectral data agreed with a structure whose mass was composed of two fucopyranosyl units.
51. T. Satoh, K. Horiguchi, Tetrahedron Lett. 1995, 36, 8235-8238.
52. M. Casillas, A. M. Gómez, J. C. López, S. Valverde, Synlett 1996, 628-630.
53. M. Hoffmann, H. Kessler, Tetrahedron Lett. 1997, 38, 1903-1906.
54. 1,7 (8.4 Hz) for 40 agreed with the S configuration at C-7 with a chair conformation of the dioxane ring.
55. G. B. Howart, D.G. Lance, W. A. Szarek, J. K. N. Jones, Can. J. Chem. 1969, 47, 75.
56. 1H NMR (200 MHz) data for 46: α = 5.50 (d, J = 5.1 Hz, 1 H), 5.32 (dd, J = 8.0, 4.0 Hz, 1 H), 5.11 (dd, J = 3.9, 4.3 Hz, 1 H), 4.60 (dd, J = 3.0, 7.5 Hz, 1 H), 4.53 (dd, J = 4.7, 3.9 Hz, 1 H), 4.34 (dd, J = 7.7, 1.7 Hz, 1 H), 3.96 (dd, J = < 1.0, 7.9 Hz, 1 H), 2.09 (s, 3 H), 2.05 (s, 3 H). For 47: α = 5.53 (d, J = 5.0 Hz, 1 H). 5.42 (dd, J = 5.0, 8.5 Hz, 1 H), 5.21 (t, J = 2.6 Hz, 1 H), 4.60 (dd, J = 2.2, 7.9 Hz, 1 H), 4.40 (dd, J=1.9 7.9 Hz, 1 H), 4.38 (dd, J = 2.7, 8.6 Hz, 1 H), 4.29 (dd, J = 2.3 5.0 Hz, 1 H), 4.26 (dd, J = 2.7, 7.6 Hz, 1 H), 4.16 (dd, J = 1.7, 5.0 Hz, 1 H), 2.08 (s, 3 H), 2.00 (s, 3 H).