Chromium(II)-complex mediated formation of C-glycosides from glycosyl halides under aqueous biphasic conditions

Tetrahedron Letters

Volumn 48, Issue 41, 2007, Pages 7351-7353

  Juhász, Zsuzsa ^a   Micskei, Károly ^a   Gál, Emese ^a   Somsák, László ^a  

^a UNIVERSITY OF DEBRECEN   (Hungary)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; CHROMIUM; GLYCOSIDE; GLYCOSYL HALIDE DERIVATIVE; HALIDE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; SYNTHESIS;

EID: 34548473301     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.08.019     Document Type: Article

References (28)

1. Reviews on the syntheses and uses of C-glycosides:. Postema M.H.D., and Calimente D. In: Wang P.G., and Bertozzi C. (Eds). Glycochemistry: Principles, Synthesis and Applications. C-Glycoside Synthesis: Recent Developments and Current Trends (2000), Marcel Dekker 77-131 Chapter 4
2. Du Y., and Linhardt R.J. Tetrahedron 54 (1998) 9913-9959
3. Levy D.E., and Fügedi P. Strategies Towards C-Glycosides. In: Levy D.E., and Fügedi P. (Eds). The Organic Chemistry of Sugars (2006), CRC Press, Boca Raton 269-348
4. Togo H., He W., Waki Y., and Yokoyama M. Synlett (1998) 700-717
5. Beau J.-M., and Gallagher T. Top. Curr. Chem. 187 (1997) 1-54
6. Nicotra F. Top. Curr. Chem. 187 (1997) 55-83
7. Postema M.H.D. C-Glycoside Synthesis (1995), CRC Press, Boca Raton
8. Levy D.E., and Tang C. The Chemistry of C-Glycosides (1995), Pergamon
9. Somsák L. Chem. Rev. 101 (2001) 81-135
10. Praly J.-P. Adv. Carbohydr. Chem. Biochem. 56 (2001) 65-151
11. Lubineau A., Augé J., and Queneau Y. Synthesis (1994) 741-760
12. Scherrmann M.C., and Lubineau A. Actual. Chimique (2003) 72-76
13. Lubineau A., and Auge J. Mod. Solv. Org. Synth. (1999) 1-39
14. Lubineau A. Chem. Ind. (1996) 123-126
15. Li C.J., and Chan T.-H. Organic Reactions in Aqueous Media (1997), John Wiley and Sons, New York
16. Kovács G., Gyarmati J., Somsák L., and Micskei K. Tetrahedron Lett. 37 (1996) 1293-1296
17. Kovács G., Tóth K., Dinya Z., Somsák L., and Micskei K. Tetrahedron 55 (1999) 5253-5264
18. Kovács G., Micskei K., and Somsák L. Carbohydr. Res. 336 (2001) 225-228
19. Micskei K., Kiss-Szikszai A., Gyarmati J., and Hajdu Cs. Tetrahedron Lett. 42 (2001) 7711-7713
20. Auge J., Gil R., and Kalsey S. Tetrahedron Lett. 40 (1999) 67-70
21. Micskei K., Juhász Z., Ratkovic Z., and Somsák L. Tetrahedron Lett. 47 (2006) 6117-6120
22. Micskei K., Debreczeni F., and Nagypál I. J. Chem. Soc., Dalton Trans. (1983) 1335-1338
23. 2O] (1.372 g, 7.29 mmol) was added in one portion. Formation of the complex was indicated by a change of colour to blue. The pH of the solution was 6.5.
24. 11 and separated by column chromatography (eluent ether/hexane = 1:1 to 3:1) to give 8a in 81% yield as pale yellow crystals.
25. Giese B., Groninger K.S., Witzel T., Korth H.G., and Sustmann R. Angew. Chem., Int. Ed. Engl. 26 (1987) 233-234
26. Giese B., Gilges S., Groninger K.S., Lamberth C., and Witzel T. Liebigs Ann. Chem. (1988) 615-617
27. Korth H.G., Sustmann R., Groninger K.S., Leisung M., and Giese B. J. Org. Chem. 53 (1988) 4364-4369
28. Gotanda K., Matsugi M., Suemura M., Ohira C., Sano A., Oka M., and Kita Y. Tetrahedron 55 (1999) 10315-10324