Synthesis of C-glycosides from glycals or vinylogous lactones and trimethylsilyl ketene acetals

Tetrahedron

Volumn 52, Issue 18, 1996, Pages 6397-6408

  Csuk, René ^a   Schaade, Martina ^b,d   Krieger, Claus ^c  

^a MARTIN LUTHER UNIVERSITY HALLE WITTENBERG   (Germany)

^b UNIVERSITY OF HEIDELBERG   (Germany)

^c MAX PLANCK INSTITUTE FOR MEDICAL RESEARCH   (Germany)

^d UNIVERSITY OF ZURICH   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

GLYCOSIDE;

ARTICLE; CRYSTALLOGRAPHY; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0029866811     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(96)00275-X     Document Type: Article

References (25)

1. Levy, D. E.; Tang, C., The Chemistry of C-Glycosides, Pergamon Press, Oxford, 1995.
2. Ireland, R. E.; Thaisrivongs, S.; Vanier, N.; Wilcox, C. S., J. Org. Chem. 1980, 45, 48.
3. Danishefsky, S. J.; DeNinno, S.; Lartey, P., J. Am. Chem. Soc. 1987, 109, 2082.
4. Tulshian, D. B.; Fraser-Reid, B., J. Org. Chem. 1984, 49, 519.
5. Danishefsky, S. J.; Uang, B. J.; Quallich, G., J. Am. Chem. Soc. 1985, 107, 1285.
6. Levy, D. E.; Dasgupta, F.; Tang, P. C., Tetrahedron: Asymmetry 1994, 5, 2265.
7. Hersovici, J.; Muleka, K.; Boumaiza, L.; Antonakis, K., J. Chem. Soc., Perkin Trans 1 1990, 1995.
8. Grynkiewicz, G.; BeMiller, J. N., Carbohydr. Res. 1982, 108, 229.
9. Isobe, M., Yuki Gosei Kagaku Kyokaishi 1994, 52, 968.
10. Orsini, F.; Pelizzoni, F.; Carbohydr. Res. 1993, 243, 183.
11. Csuk, R.; Glänzer, B. I., J. Carbohydr. Chem. 1990, 9, 809.
12. Csuk, R.; Schaade, M., Tetrahedron 1994, 50, 3333.
13. Csuk, R.; Schaade, M.; Schmidt, A., Tetrahedron 1994, 50, 11885.
14. Prepared from 2,3,4,6-tetra-O-benzoyl-D-glucopyranosyl bromide by treatment with zinc-silver/ graphite in 89% yield according to Csuk, R.; Fürstner, A.; Glänzer, B. I.; Weidmann, H., J. Chem. Soc., Chem. Commun. 1986, 1149.
15. This does not seem very surprising due to a possible complexation of the Lewis acid by the solvent; cf. ref. 5
16. Acetonitrile has been reported to favour the formation of α-glycosides (cf. Schmidt, R. R.; Rücker, E., Tetrahedron Lett. 1980, 21, 1421) due to the generation of an intermediary isonitrilium ion; for the TMSOTf catalyzed reaction of 13 with 2, however, such an effect could be observed.
17. Interesting to note that for all pairs of anomeric C-glycosides in this work it was observed that the β-anomers were less polar than the α-anomers during chromatography on silica gel (hexane/ethyl acetate 10:1) and thus eluted first; cf. refs cited in 5 and 17.
18. G. B. Stothers, Carbon-13 NMR Spectroscopy, Academic Press, New York, 1973, Chapter 3.
19. Chmielewski, M.; BeMiller, J. N.; Ceretti, D. P., J. Org. Chem. 1981, 46, 3903.
20. Bratka, M.; Farr, R. N.; Chaguir, B.; Massiot, G.; Lavaud, C.; Anderson, W. R.; Sinou, D.; Davies, G. D., J. Org. Chem. 1993, 58, 2992.
21. A similar effect would be expected for H-C(3); this effect, however, is much less pronounced (|δΔ| = 0.03-0.05 ppm) and thus the comparison of δ H-C(3) of the different anomers can not be regarded as an unambiguous criterion for the assignment of the configuration.
22. The atomic coordinates, bond lengths and angles, torsion angles and thermal parameters are available on request from the Director of the Cambridge Crystallographic Centre, University Chemical Laboratory, Lensfield Road, Cambridge CB21EW. Any request should be accompanied by the full literature citation for this communication.
23. 13C NMR spectra both products show β-configuration at the anomeric center and differ only in the absolute configuration at C(2).
24. The formation of two products from the reaction of 28 with 2 is similar to the reported reaction of 28 with ethyl 2-lithio-[1,3]-dithiolane-2-carboxylate; cf. Paulsen, H.; Bünsch, H., Chem. Ber. 1978, 111, 3484.
25. Paulsen, H.; Köbernick, W., Chem. Ber. 1977, 110, 2127.