New chiral building blocks and branched 1,6-anhydro sugars from regio- and stereoisomeric Černý epoxides

European Journal of Organic Chemistry

Volumn , Issue 21, 2005, Pages 4557-4562

  Krohn, Karsten ^a   Gehle, Dietmar ^a   Flörke, Ulrich ^a  

^a UNIVERSITY OF PADERBORN   (Germany)

Author keywords

1,6 Anhydro sugars; Branched sugars; ern epoxides; Chiral building blocks; Epoxide rearrangement; Gilman cuprates; Vinyl tosylate cross coupling

Indexed keywords

EID: 27644521950     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/ejoc.200500242     Document Type: Article

References (27)

1. K. Krohn, D. Gehle, U. Flörke, Eur. J. Org. Chem. 2005, 2841-2848.
2. M. Černý, V. Gut, J. Pacak, Collect. Czech. Chem. Commun. 1961, 26, 2542-2550.
3. S. Czernecki, C. Leteux, A. Veyrieres, Tetrahedron Lett. 1992, 33, 221-224.
4. M. Samadi, C. Munoz-Letelier, S. Poigny, M. Guyot, Tetrahedron Lett. 2000, 41, 3349-3353.
5. F. Kato, M. Kato, F. Tsukamoto, M. Tsukamoto (Ishihara Sangyo Kaisha, Japan), JP 07188205, December 27, 1993; Chem. Abstr. 1995, 124, 30251.
6. K. Okano, T. Ebata, K. Koseki, H. Kawakami, K. Matsumoto, H. Matsushita, Chem. Pharm. Bull. 1993, 41, 861-865.
7. S. Mizukoshi, F. Kato, M. Tsukamoto, K. Mizukoshi, S. Kon (Ishihara Sangyo Kaisha Ltd., Japan), JP 2087805, January 21, 1993; Chem. Abstr. 1994, 121, 149078.
8. S. Mizukoshi, F. Kato, M. Tsukamoto, K. Kon (Ishihara Sangyo Kaisha, Ltd., Japan), EP 560055, February 5, 1993; Chem. Abstr. 1994, 121, 9922.
9. F. Kato, M. Kato, F. Tsukamoto, M. Tsukamoto (Ishihara Sangyo Kaisha, Japan) JP 08059646, August 12, 1994; Chem. Abstr. 1996, 125, 11351.
10. S. Mizukoshi, F. Kato, M. Tsukamoto (Jpn. Kokai Tokkyo Koho) JP 06080565, March 22, 1994; Chem. Abstr. 1994, 121, 149078.
11. M. Černý, J. Pacak, J. Stanek, Collect. Czech. Chem. Commun. 1965, 30, 1151-1157.
12. J. Dolezalova, T. Trnka, M. Cerny, Collect. Czech. Chem. Commun. 1982, 47, 2415-2422.
13. Z. J. Witczak, Levoglucosenone and Levoglucosans. Chemistry and Applications, in: Froniers in Biomedicine and Biotechnology, vol. 2, ATL PRESS, Mount Prospect, USA, IL, 1994.
14. M. Černý, J. J. Stanek, Adv. Carbohydr. Chem. Biochem. 1977, 34, 23-177.
15. S. S. Kulkarni, J.-C. Lee, S.-C. Hung, Curr. Org. Chem. 2004, 8, 475-509.
16. A. Fürst, P. A. Plattner, in 12th Internat. Congress of Pure and Applied Chemistry, New York, 1951, p. 409.
17. A. F. Sviridov, D. V. Yashunskii, M. S. Ermolenko, N. K. Kochetkov, Izv. Akad. Nauk SSSR, Ser. Khim. 1984, 723-725.
18. K. M. Belyk, W. R. Leonard, Jr., D. R. Bender, D. L. Huges, J. Org. Chem. 2000, 65, 2588-2590.
19. D. Cai, D. L. Hughes, T. R. Verhoeven, Tetrahedron Lett. 1996, 37, 2537-2540.
20. K. Krohn, D. Gehle, O. Kamp, T. van Ree, J. Carbohydr. Chem. 2003, 22, 377-383.
21. H. M. Bradley, R. G. Jones, D. W. Knight, Synlett 1992, 479-480.
22. J. Thiem, A. Prahst, I. Lundt, Liebigs Ann. Chem. 1986, 1044-1056.
23. M. Černý, L. Kalvoda, J. Pacak, Collect. Czech. Chem. Commun. 1968, 33, 1143-1156.
24. M. Černý, I. Buben, J. Pacak, Collect. Czech. Chem. Commun. 1963, 28, 1569-1575.
25. CCDC-267820 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.
26. Bruker (2002), SMART (Version 5.62), SAINT (Version 6.02), SHELXTL (Version 6.10) and SADABS (Version 2.03), Bruker AXS Inc., Madison, Wisconsin, USA.
27. H. D. Flack, Acta Cryst. 1983, A39, 876-881.