Stereoselective synthesis of 2-deoxy-β-glycosides from glycal precursors. 2. Stereochemistry of glycosidation reactions of 2-thiophenyl- and 2-selenophenyl-α-D-gluco-pyranosyl donors

Tetrahedron

Volumn 53, Issue 26, 1997, Pages 8837-8852

  Roush, William R ^a   Sebesta, David P ^a   James, Ray A ^a  

^a INDIANA UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

GLUCOSE DERIVATIVE; GLYCOSIDE; MITHRAMYCIN; OLIVOMYCIN;

ARTICLE; CHEMICAL STRUCTURE; GLYCOSYLATION; MOLECULAR STABILITY; PRIORITY JOURNAL; STEREOCHEMISTRY; SYNTHESIS;

EID: 0030843605     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)90395-1     Document Type: Article

References (56)

1. Remers, W. A. In The Chemistry of Antitumor Antibiotics; Wiley-Interscience: New York 1979; pp 133-175.
2. Remers, W. A.; Iyengar, B. S. In Cancer Chemotherapeutic Agents; W. O. Foye, Ed.; ACS: 1995; pp 578.
3. Lee, M. D.; Dunne, T. S.; Chang, C. C.; Siegel, M. M.; Morton, G. O.; Ellestad, G. A.; McGahren, W. J.; Borders, D. B. J. Am. Chem. Soc. 1992, 114, 985.
4. Nicolaou, K. C.; Dai, W.-M. Angew. Chem., Int. Ed. Engl. 1991, 30, 1387.
5. Henderson, F. G. In Digitalis; C. Fish and Surawicz, Eds.; Grune and Stratton: New York, 1969; pp 3-21.
6. Rohr, J.; Thiericke, R. Nat. Prod. Rep. 1992, 9, 103.
7. Weber, S.; Zolke, C.; Rohr, J.; Beale, J. M. J. Org. Chem. 1994, 59, 4211.
8. Muntwyler, R.; Keller-Schierlein, W. Helv. Chim. Acta 1972, 55, 2071.
9. Mallams, A. K.; Puar, M. S.; Rossman, R. R.; McPhail, A. T.; Macfarlane, R. D.; Stephens, R. L. J. Chem. Soc., Perkin Trans. I 1983, 1497.
10. Thiem, J.; Klaffke, W. Topics Curr. Chem. 1990, 154, 285.
11. Toshima, K.; Tatsuta, K. Chem. Rev. 1993, 93, 1503.
12. Roush, W. R.; Lin, X.-F. J. Am. Chem. Soc. 1995, 117, 2236.
13. Roush, W. R.; Michaelides, M. R.; Tai, D. F.; Lesur, B. M.; Chong, W. K. M.; Harris, D. J. J. Am. Chem. Soc. 1989, 111, 2984.
14. Roush, W. R.; Murphy, M. J. Org. Chem. 1992, 57, 6622.
15. Sebesta, D. P.; Roush, W. R. J. Org. Chem. 1992, 57, 4799.
16. Roush, W. R.; Briner, K.; Kesler, B. S.; Murphy, M.; Gustin, D. J. J. Org. Chem. 1996, 61, 6098.
17. Hunt, J. A.; Roush, W. R. J. Am. Chem. Soc. 1996, 118, 9998.
18. Danishefsky, S. J.; Bilodeau, M. T. Angew. Chem., Int. Ed. Engl. 1996, 35, 1380.
19. Gao, X.; Mirau, P.; Patel, D. J. J. Mol. Biol. 1992, 223, 259.
20. Sastry, M.; Patel, D. J. Biochemistry 1993, 32, 6588.
21. Walker, S.; Valentine, K. G.; Kahne, D. J. Am. Chem. Soc. 1990, 112, 6428.
22. Silva, D. J.; Kahne, D. E. J. Am. Chem. Soc. 1993, 115, 7962.
23. Silva, D. J.; Goodnow, R., Jr.; Kahne, D. Biochemistry 1993, 32, 463.
24. Silva, D. J.; Kahne, D.; Kraml, C. M. J. Am. Chem. Soc. 1994, 116, 2641.
25. Horton, D.; Priebe, W.; Sznaidman, M. Carbohydr. Res. 1990, 205, 71.
26. Ito, Y.; Ogawa, T. Tetrahedron Lett. 1987, 28, 2723.
27. Ramesh, S.; Franck, R. W. J. Chem. Soc., Chem. Commun. 1989, 960.
28. Grewal, G.; Kaila, N.; Franck, R. W. J. Org. Chem. 1992, 57, 2084.
29. Preuss, R.; Schmidt, R. R. Synthesis 1988, 694.
30. Perez, M.; Beau, J.-M. Tetrahedron Lett. 1989, 30, 75.
31. Overend, W. G.; Rees, C. W.; Sequeira, J. S. J. Chem. Soc. 1962, 3429.
32. Buncel, E.; Bradley, P. R. Can. J. Chem. 1967, 45, 515.
33. Roush, W. R.; Sebesta, D. P.; Bennett, C. E. Tetrahedron 1997, preceding paper in this issue.
34. Ito, Y.; Ogawa, T. Tetrahedron 1990, 46, 89.
35. Jaurand, G.; Beau, J.-M.; Sinaÿ, P. J. Chem. Soc., Chem. Commun. 1981, 572.
36. For example, use of the acetate derivative of 8c (e.g., i) as a donor in the reaction with cholesterol gave non-reproducible results. In several experiments, the β-glucoside ii was obtained with selectivity of 3-6 : 1, however in one case the α-mannoside iii predominated (4 : 1 selectivity). This reflects the dependence of these glycosidations on subtle variations in reaction conditions. (equation presented) i several runs: 3-6 : 1 selectivity ii R = cholesteryl iii one run: 1 : 4 selectivity
37. Fürst, A.; Plattner, P. A. In Abstr. of Papers, 12th Intern. Congr. Pure Appl. Chem.; New York, 1951; pp 409.
38. Fürst, A.; Scotoni, R., Jr. Helv. Chim. Acta 1953, 1332 and 1410.
39. Angyal, S. J. Chem. Ind. (London) 1954, 1230.
40. Eliel, E. L.; Allinger, N. L.; Angayal, S. J.; Morrison, G. A. Conformational Analysis; Wiley Interscience: New York, 1965.
41. Cherest, M.; Felkin, H.; Prudent, N. Tetrahedron Lett. 1968, 2199.
42. Anh, N. T.; Eisenstein, O. Nouv. J. Chim. 1977, 1, 61.
43. Schmidt, R. R. Angew. Chem., Int. Ed. Engl. 1986, 25, 212.
44. Schmidt, R. R. In Comprehensive Organic Synthesis; B. M. Trost, Ed.; Wiley: 1991; Vol. 6; pp 33-64.
45. Zimmermann, P.; Greilich, U.; Schmidt, R. R. Tetrahedron Lett. 1990, 31, 1849.
46. Urban, F. J.; Moore, B. S.; Breitenbach, R. Tetrahedron Lett. 1990, 31, 4421.
47. Evans, D. A.; Kaldor, S. W.; Jones, T. K.; Clardy, J.; Stout, T. J. J. Am. Chem. Soc. 1990, 112, 7001.
48. Garegg, P. J.; Hultberg, H.; Wallin, S. Carbohydr. Res. 1982, 108, 97.
49. 2, 4Å sieves, -78°C; ≥98% recovery).
50. Nicolaou, K. C.; Ladduwahetty, T.; Randall, J. L.; Chucholowski, A. J. Am. Chem. Soc. 1986, 108, 2466.
51. Jones, D. K.; Liotta, D. C. Tetrahedron Lett. 1993, 34, 7209.
52. Murphy, M. Ph. D. Thesis, Indiana University, 1993.
53. 1H NMR analysis) for use in subsequent reactions.
54. 3CN, 23°C, 24 h).
55. 3CN, 23°C, 36-48 h, 83% yield).
56. Acceptor 44 was prepared by desilylation of glycal 5d (HF-pyridine, THF, 0°C, 96% yield). (equation presented)