Condensation of D-mannosaldehyde derivatives with ethyl diazoacetate. An easy and stereoselective chain elongation methodology for carbohydrates: Application to new syntheses for KDO and 2-deoxy-β-KDO

Tetrahedron

Volumn 53, Issue 9, 1997, Pages 3325-3346

  López Herrera, Fidel J ^a   Sarabia García, Francisco ^a  

^a UNIVERSITY OF MÁLAGA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

3 DEOXY MANNO OCTULOSONIC ACID;

ARTICLE; CALCULATION; CARBOHYDRATE SYNTHESIS; DRUG STRUCTURE; IN VITRO STUDY; MASS SPECTROMETRY; METHODOLOGY; MOLECULAR DYNAMICS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY; THEORY; THERMODYNAMICS;

EID: 0031550815     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)00056-2     Document Type: Article

References (64)

1. Tetrahedron, Vol. 53, No. 9, pp. 3325-3346, 1997 Condensation Fidel J. López-Herrera * and Francisco Sarabia-García Departamento de Bioquímica, Biología Molecular y Química Orgánica, Facultad de Ciencias Universidad de Málaga. 29071 Málaga, Spain.
2. 1. a) Gutsche, C.D., Organic Reactions, 1954, 8, 364.
3. b) ibid, 1968, 18, 364.
4. c) Eistert, B.; Regitz, M. Methoden Org. Chem. (Houben-Weyl), 1976, 7/2b, 1852.
5. d) Wovkulich, P. M. Comprehensive Organic Synthesis, Pergamon Press, 3, 843.
6. 2. a) Wenkert, E.; McPherson, C. A. J. Am. Chem. Soc., 1972, 94, 8084.
7. b) Schöllkopf, U.; Bánhidai, B.; Frasnelli, H.; Meyer, R.; Beckhaus, H. Justus Leibigs Ann. Chem., 1974, 1767.
8. c) Schöllkopf, U.; Scholz, H-U. Synthesis, 1976, 271.
9. d) Nagao, K.; Chiba, M.; Kim, S-W. Synthesis, 1983, 197.
10. e) Singh, A. K.; Bakshi, R. K.; Corey, E. J. J. Am. Chem. Soc., 1987, 109, 6187.
11. f) Pellicciari, R.; Sisani, E.; Fringnelli, R. Tetrahedron Lett., 1980, 21, 4039.
12. g) Pellicciari, R.; Natalini, B.; Ceccheti, S.; Fringnelli, R. J. Chem. Soc. Perkin Trans 1, 1985, 493.
13. h) Pellicciari, R.; Natalini, B.; Fringnelli, R. Steroids, 1987, 49, 433.
14. i) Ye, T.; McKervey, M. A. Tetrahedron, 1992, 48, 8007.
15. 3. a) López-Herrera, F. J.; Valpuesta Fernández ,M.; García Claros, S. Tetrahedron, 1990, 46, 7165.
16. b) López-Herrera, F. J.; Sarabia-García, F.; Pino-González, M. S. Tetrahedron Lett., 1994, 35, 2933.
17. 4. a) López-Herrera, F. J;. Sarabia-García, F. Tetrahedron Lett., 1994, 35, 6705.
18. b) Sarabia-García, F.; López-Herrera, F. J.; Pino-González, M. S. Tetrahedron Lett., 1994, 35, 6709.
19. 5. a) López-Herrera, F. J.; Sarabia-García, F. Tetrahedron Lett., 1993, 34, 3467.
20. b) ibid, 1994, 35, 2929.
21. 6. López-Herrera, F. J.; Sarabia-García, F. Tetrahedron Lett., 1994, 35, 6705.
22. 7. López-Herrera, F. J.; Sarabia-García, F. Tetrahedron Lett., 1995, 36, 2851.
23. 8. a) Levin, D. H.; Racker, E. J. Biol. Chem., 1959, 234, 2532.
24. b) Unger, F.M. Adv. Carbohydr. Chem. Biochem., 1981, 38, 323.
25. 9. a) Claesson, A.; Luthman, K.; Gustafsson, K.; Bondesson, G. Biochem. Biophys. Res. Commun., 1987,143, 1063.
26. b) Goldman, R.; Kohlbrenner, W.; Lartey, P.; Pernet, A. Nature, 1987, 329, 162.
27. 10. a) Kochetkov, N. K.; Dimitriev, B. A.; Backinowsky, L. V. Carbohydr. Res., 1967, 5, 339.
28. b) Danishefsky, S. J.; Pearson, W. H.; Segmuller, B. E. J. Am. Chem. Soc., 1985, 107, 1280.
29. c) Imoto, M.; Kusumoto, S.; Shiba, T. Tetrahedron Lett., 1987, 28, 6235.
30. d) Branchaud, B. P.; Meier, M. S. J. Org. Chem., 1989, 54, 1320.
31. e) van der Klein, P.A.M.; Boons, G.J.P.H.; Veeneman, G.H.; van der Marel, G.A.; van Boom, J.H. Tetrahedron Lett., 1989, 30, 5477.
32. f) Esswein, A.; Betz, R.; Schmidt, R. R. Helv. Chim. Acta, 1989, 72, 213.
33. g) Ramage, R.; McLeod, A. M.; Rose, G. W. Tetrahedron, 1991, 47, 5625.
34. h) Donodoni, A.; Merino, P. J. Org. Chem., 1991, 56, 5294.
35. i) Martin, S. F.; Zinke, P. W. J. Org. Chem., 1991, 56, 6600.
36. j) Giese, B.; Linker, T. Synthesis, 1992, 46.
37. k) Smith, D. B.; Wang, Z.; Schreiber, S. L. Tetrahedron, 1990, 46, 4793.
38. l) Lubineau, A.; Augé, J.; Lubin, N. Tetrahedron, 1993, 49, 4639.
39. ll) Bednarski, M. D.; Crans, D. C.; DiCosimo, R.; Simon, E. S.; Stein, P. D.; Whitesides, G. M.; Schneider, M. J. Tetrahedron Lett, 1988, 29, 427.
40. m) Coutrot, P.; Grison, C.; Tabyaoui, M. Tetrahedron Lett., 1993, 34, 5089.
41. n) Dondoni, A.; Marra, A.; Merino, P. J. Am. Chem. Soc., 1994, 116, 3324.
42. o) Sugai, T.; Shen, G-J.; Ichikawa, Y.; Wong, C-H. J. Am. Chem. Soc., 1993, 115, 413.
43. 11. a) Luthman, K.; Orbe, M.; Waglund, T.; Claesson, A. J. Org. Chem., 1987, 52, 3777.
44. b) Claesson, A. J. Org. Chem., 1987, 52, 4414.
45. c) Boons, G.J.P.H.; van Delft, F. L.; van der Klein, P.A.M.; van der Marel, G. A.; van Boom, J.H. Tetrahedron, 1992, 48, 885.
46. d) Ohrui, H.; Morita, M.; Meguro, H. Carbohydr. Res., 1992, 224, 319.
47. e) Lubineau, A.; Augé, J.; Lubin, N. Tetrahedron, 1993, 49, 4639.
48. 12. Ikota, N.; Takamura, N.; Young, S. D.; Ganem, B. Tetrahedron Lett., 1981, 22, 4163.
49. 13. Wolfrom, M. L.; Thompson, A. Methods in Carbohydr. Chem. vol. 2, p 427, Academic Press Inc.
50. 14. a) Burker, U.; Allinger, N. L. Molecular Mechanics, ACS Monograph 177, Washington D.C., 1982.
51. b) Clark, T. A Handbook of Computational Chemistry. A Practical Guide to Chemical Structure and Energy Calculations, John-Wiley and Sons, N. Y., 1985.
52. 15. Itoh, H.; Kaneko, T.; Tanami, K.; Yoda, K. Bull. Chem. Soc. Jpn., 1988, 61, 3356.
53. 16. Shing, T. K. M. Tetrahedron, 1992, 48, 6777.
54. 17. The synthesis of the mannose aldehyde 8 was performed according to the following procedure: To a solution of 12 mL of benzyl bromide in 172 mL of anhydrous DMF was added in one portion 3.22 g of 80% sodium hydride. The suspension was cooled at 0°C and 4.3 g of D-mannose Diethyl dithioacetal was slowly added to the stirred mixture. The resulting suspension was vigorously stirred for 2h 30 min. and after this time, methanol was added dropwise to destroy the excess of sodium hydride. Finally, the solution was diluted with 500 mL of water and extracted with ter-butyldimethyl ether (3x1). The combined organic layers were washed with water, dried with anhydrous sodium sulphate, filtered and concentrated. The crude obtained (12g) was dissolved in 75 mL of acetone and 18 mL of water. This solution was treated with 13 g of cadmiun carbonate and a solution of 13 g of mercury chloride in 15 mL of acetone. After 2 h, the reaction was complete, then the suspension was filtered and the filtrate was concentrated and extracted with chloroform (4x1). The organic solution was washed with water, dried and concentrated to obtain 6.7 g of the pure aldehyde 8 (76%).
55. 18. a) Nicotra, F.; Ronchetti, F.; Russo, G.; Toma, L. Tetrahedron Lett., 1984, 25, 5697-5700,
56. b) Fréchou, C.; Dheilly, L.; Beaupére, D.; Uzan, R.; Demailly, G. Tetrahedron Lett., 1992, 33, 5067.
57. 19. Setoi, H.; Takeno, H.; Hashimoto, M. Tetrahedron Lett., 1985, 26, 4617.
58. 20. Haudrechy, A.; Sinaÿ, P. J. Org. Chem., 1992, 57, 4142.
59. 21. Hürzeler, M.; Bernet, B.; Mäder, T.; Vasella, A. Helv. Chim Acta, 1993, 76, 1779.
60. 22. Horton, D.; Jewell, J. S. Carbohydr. Res., 1966, 2, 251.
61. 23. Ohrui, H.; Jones, G. H.; Moffat, J. G.; Maddox, M. L.; Christensen, A. T.; Byram, S. K. J. Am. Chem. Soc., 1975, 97, 4602.
62. 24. a) Hershberger, C.; Davis, M.; Binkley, S. B. J. Biological Chem., 1968, 245, 1585.
63. b) McNicholas, P. A.; Batley, M.; Redmond, J. W. Carbohydr. Res., 1987, 165, 17.
64. 4 purchased from SIGMA-ALDRICH, Ref. K-7000.