MICHAEL-type additions in the synthesis of α-O- and -S-2-deoxyglycosides

Tetrahedron Letters

Volumn 37, Issue 20, 1996, Pages 3453-3456

  Michael, Katja ^a   Kessler, Horst ^a  

^a TECHNICAL UNIVERSITY OF MUNICH   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

GLYCOSIDE;

ARTICLE; CARBOHYDRATE SYNTHESIS; CHIRALITY; REACTION ANALYSIS;

EID: 0029999934     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00616-8     Document Type: Article

References (27)

1. Anthracycline Antibiotics; El Khadem, H. S. Ed.; Academic Press, New York, 1982.
2. Lee, M. D.; Dunne; T. S.; Chang, C. C.; Ellestad, G. A.; Siegel, M. M.; Morton, G. O.; McGahren, W. J.; Borders, D. B. J. Am. Chem. Soc. 1987, 109, 3466-3468.
3. Roush, W. R.; Lin, X.-F. J. Org. Chem. 1991, 56, 5740-5742.
4. Thiem, J.; Klaffke, W. Top. Curr. Chem. 1990, 154, 286-332.
5. Friesen, R. W.; Danishefsky, S. J. Tetrahedron 1990, 46, 103-112.
6. Kessler, H.; Kling, A.; Kottenhahn, M. Angew. Chem. Int. Ed. Engl. 1990, 102, 452-454.
7. Kottenhahn, M.; Kessler, H. Liebigs Ann. Chem. 1991, 727-744.
8. Bolitt, V.; Mioskowski, C.; Lee, S.-G.; Falck, J. R. J. Org. Chem. 1990, 55, 5812-5813.
9. Sabesan, S.; Neira, S. J. Org. Chem. 1991, 56, 5468-5472.
10. Petit, J.-M.; Paquet, F.; Beau, J.-M. Tetrahedron Lett. 1991, 32, 6125-6128.
11. Kessler, H.; Michael, K.; Kottenhahn, M. Liebigs Ann. Chem. 1994, 811-816.
12. Kolar, C.; Kneißl, G. Angew. Chem. Int. Ed. Engl. 1990, 29, 809-811.
13. Ferner, R. J. Adv. Carbohydr. Chem. Biochem. 1969, 24, 199-266.
14. 4-catalysis, no addition product was observed. Instead, regioselective cleavage of the axial benzyl group at C-4 took place. (figure presented)
15. Holder, N. L. Chem. Rev. 1982, 82, 287-332.
16. Kirschning, A.; Dräger, G.; Hardes, J. Synlett 1993, 289-290.
17. Fraser-Reid, B.; Walker, D. L.; Tam, S. Y. K.; Holder, N. L. Can J. Chem. 1973, 51, 3950-3954.
18. Brimacombe, J. S. A. Angew. Chem. Int. Ed. Engl. 1969, 8, 401-409.
19. Paulsen, H.; Koebernick, W.; Koebernick, H. Tetrahedron Lett. 1976, 2297-2300.
20. Pelyvás, I; Sztaricskai, F.; Bognár, R. Carbohydr. Res. 1979, 76, 419-425.
21. Pelyvás, I.; Hasegawa, A.; Whistler, R. L. Carbohydr. Res. 1986, 146, 193-203.
22. The reactions under DBU catalysis were carried out without solvent in an ultrasonic bath at 70°C for 2h.
23. For the reactions under KCN/18-crown-6 catalysis dichloromethane was used as a solvent just enough to dissolve the reactants.
24. 2); 4.58 (1H, m, H-5); 4.44-4.23 (2H, m, H-6, H-6′); 3.22, 3.06 (2H, m, H-β, H-β′); 3.16 (1H, m, H-2); 2.66 (1H, d, H-2′); 2.18, 2.08 (2 · 3H, 2s, 2 OAc) ppm.
25. Evans, D. A.; Truesdale, L. K.; Grimm, K. G.; Nesbitt, S. L. J. Am Chem Soc. 1977, 99, 5009-5017.
26. Luche, J.-L., J. Am. Chem. Soc. 1978, 100, 2227-2228.
27. Rücker, G; Hötter, H; Grajewski, W. Synth. Commun. 1980, 10, 623-626.