Reactivity of per-O-acetylated 1-thioglycosides and glycosyl sulfones towards chromium(II) complexes in aqueous medium

Tetrahedron Letters

Volumn 47, Issue 34, 2006, Pages 6117-6120

  Micskei, Károly ^a   Juhász, Zsuzsa ^a   Ratković, Zoran R ^b   Somsák, László ^a  

^a UNIVERSITY OF DEBRECEN   (Hungary)

^b UNIVERSITY OF KRAGUJEVAC   (Serbia)

Author keywords

[No Author keywords available]

Indexed keywords

CARBON; CHROMIUM DERIVATIVE; GLYCOSIDE; SUGAR; SULFONE; SULFUR;

ACETYLATION; AQUEOUS SOLUTION; ARTICLE; CHEMICAL ANALYSIS; CHEMICAL BOND; CHEMICAL REACTION KINETICS; COMPLEX FORMATION; REACTION ANALYSIS;

EID: 33746001926     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.06.075     Document Type: Article

References (29)

1. Collins P.M., and Ferrier R.J. Monosaccharides-Their Chemistry and Their Roles in Natural Products (1995), John Wiley & Sons, Chichester
2. Praly J.-P. Adv. Carbohydr. Chem. Biochem. 56 (2001) 65-151
3. Somsák L. Chem. Rev. 101 (2001) 81-135
4. Lubineau A., Augé J., and Queneau Y. Synthesis (1994) 741-760
5. Scherrmann M.C., and Lubineau A. Actualite Chimique (2003) 72-76
6. Lubineau, A.; Auge, J. Water as solvent in organic synthesis. Modern Solvents in Organic Synthesis, 1999; pp 1-39.
7. Lubineau A. Chem. Ind. (1996) 123-126
8. Kovács G., Gyarmati J., Somsák L., and Micskei K. Tetrahedron Lett. 37 (1996) 1293-1296
9. Kovács G., Tóth K., Dinya Z., Somsák L., and Micskei K. Tetrahedron 55 (1999) 5253-5264
10. Kovács G., Micskei K., and Somsák L. Carbohydr. Res. 336 (2001) 225-228
11. Reviews:. Wessjohann L.A., and Scheid G. Synthesis (1999) 1-36
12. Fürstner A. Chem. Rev. 99 (1999) 991-1045
13. Hodgson D.M. J. Organomet. Chem. 476 (1994) 1-5
14. Cintas P. Synthesis (1992) 248-257
15. Pouilly P., Chénedé A., Mallet J.-M., and Sinaÿ P. Tetrahedron Lett. 33 (1992) 8065-8068
16. Skrydstrup T., Mazéas D., Elmouchir M., Doisneau G., Riche C., Chiaroni A., and Beau J.-M. Chem. Eur. J. 3 (1997) 1342-1356
17. Zhang Z., and Magnusson G. Carbohydr. Res. 295 (1996) 41-56
18. Mereyala H.B., and Reddy G.V. Tetrahedron 47 (1991) 6435-6448
19. Zinner H., and Peseke K. Chem. Ber. 98 (1965) 3515-3519
20. Zinner H., and Peseke K. Chem. Ber. 98 (1965) 3508-3514
21. NMR data:. Khodair A.I., Al-Masoudi N.A., and Gesson J.-P. Nucleosides, Nucleotides, Nucleic Acids 22 (2003) 2061-2076
22. Collins P.M. J. Chem. Soc. Perkin Trans. 1 (1974) 1069-1075
23. Wagner G. Arch. Pharm. Ber. Deutsch. Pharm. Ges. 296 (1963) 576-584
24. Skrydstrup T., Mazéas D., Elmouchir M., Doisneau G., Riche C., Chiaroni A., and Beau J.-M. Chem. Eur. J. 3 (1997) 1342-1356
25. 1H NMR.
26. Micskei K., Debreczeni F., and Nagypál I. J. Chem. Soc., Dalton Trans. (1983) 1335-1338
27. 9 except for the amounts of KOH, which were: 6.25-4.0-2.0-0 ml (entries 2-5, Table 2), and the amount of the ligand EDTA was 8.15 mmol (3.035 g) in all cases.
28. 13 in ∼40% yield.
29. Gotanda K., Matsugi M., Suemura M., Ohira C., Sano A., Oka M., and Kita Y. Tetrahedron 55 (1999) 10315-10324