Synthesis of enantiopure C-glycosides and pseudo C-glycosides: Lewis- acid mediated heterolysis of methyl acetals

Tetrahedron Letters

Volumn 40, Issue 35, 1999, Pages 6359-6363

  Gaertzen, Oliver ^a   Misske, Andrea M ^a   Wolbers, Peter ^a   Hoffmann, H M R ^a  

^a LEIBNIZ UNIVERSITY HANNOVER   (Germany)

Author keywords

Asymmetric synthesis; C glycosides; Glycoheptopyranuronic acids; Natural product synthesis

Indexed keywords

ACETAL DERIVATIVE; GLYCOSIDE; METHYL GROUP;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; ENANTIOMER; ESTERIFICATION; LYSIS; SYNTHESIS;

EID: 0033609873     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01224-1     Document Type: Article

References (24)

1. Recent reviews on C-glycosides: (a) Hosomi, A.; Sakata, Y; Sakurai, H. Carbohydr. Res. 1987, 171, 223;
2. (b) Jaramillo, C.; Knapp, S. Synthesis 1994, 1;
3. (c) Postema, M. H. D. C-Glycoside Synthesis; CRC Press Inc.: Boca Raton, Fl, 1995;
4. Postema, M. H. D. Tetrahedron 1992, 48, 8545;
5. (d) Levy, D. E.; Tang, C. The Chemistry of C-Glycosides; Pergamon Press: Tarrytown, 1995;
6. (e) Bertozzi, C.; Bednarski, M. In Modem Methods in Carbohydrate Synthesis; Khan, S. H.; O'Neill, R. A., Eds.; Harwood: Amsterdam, 1996; p. 319;
7. (f) Nicotra, F. In Carbohydrate Chemistry; Boons, G.-J., Ed.; Blackie Academic & Professional, Thomson Science: London, New York, 1998.
8. (a) Hosomi, A.; Sakata, Y; Sakurai, H. Tetrahedron Lett. 1984, 25, 2383;
9. (b) Brown, D. S.; Bruno, M.; Davenport, R. J.; Ley, S. V. Tetrahedron 1989, 45, 4293;
10. (c) Schmidt, R. R.; Michel, J. Angew. Chem. 1980, 92, 763; for a recent application, see: Scheffler, G.; Schmidt, R. R. J. Org. Chem. 1999, 64, 1319, and references cited therein.
11. (c) Schmidt, R. R.; Michel, J. Angew. Chem. 1980, 92, 763; for a recent application, see: Scheffler, G.; Schmidt, R. R. J. Org. Chem. 1999, 64, 1319, and references cited therein.
12. We ourselves have investigated a new method to single-isomer deoxygenated and alkylated C-glycosidic acids starting from anomeric [3.3.1] oxabicyclic lactones: Gaertzen, O.; Misske, A. M.; Wolbers, P.; Hoffmann, H. M. R. Synlett 1999, 1041.
13. Giese, B.; Dupuis, J. Angew. Chem. 1983, 95, 633; Angew. Chem., Int. Ed. Engl. 1983, 22, 622.
14. Giese, B.; Dupuis, J. Angew. Chem. 1983, 95, 633; Angew. Chem., Int. Ed. Engl. 1983, 22, 622.
15. See Ref. 2a and Bennek, J. A.; Gray, G. R. J. Org. Chem. 1987, 52, 892; for a recent example, see: Jégou, A.; Pacheco, C.; Veyrières, A. Tetrahedron 1998, 54, 14779.
16. See Ref. 2a and Bennek, J. A.; Gray, G. R. J. Org. Chem. 1987, 52, 892; for a recent example, see: Jégou, A.; Pacheco, C.; Veyrières, A. Tetrahedron 1998, 54, 14779.
17. Wolbers, P.; Hoffmann, H. M. R. Tetrahedron 1999, 55, 1905.
18. (a) Lampe, T. F. J.; Hoffmann, H. M. R. J. Chem. Soc., Chem. Comm. 1996, 1931;
19. (b) Weiss, J. M.; Hoffmann, H. M. R. Tetrahedron: Asymmetry 1997, 8, 3913;
20. (c) Misske, A. M.; Hoffmann, H. M. R. Tetrahedron 1999, 55, 4315.
21. The stereochemical notation follows the convention of H. Maehr. Racemates are drawn with joists, whereas enantiopure compounds are designated with wedges: Maehr, H. J. Chem. Ed. 1985, 62, 114.
22. Wolbers, P.; Misske, A. M.; Hoffmann, H. M. R. Tetrahedron Lett. 1999, 40, 4527.
23. +): 332.1988, found: 332.1987.
24. N2′ mechanism. The benzyloxy moiety serves as leaving group: (equation presented)