A convenient access to the 1,5-anhydro forms of d-tagatose, l-rhamnulose and d-xylulose via 2-hydroxyglycal esters

Tetrahedron Asymmetry

Volumn 20, Issue 6-8, 2009, Pages 952-960

  Jarglis, Pan ^a   Göckel, Volker ^a   Lichtenthaler, Frieder W ^a  

^a DARMSTADT UNIVERSITY OF TECHNOLOGY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ESTER; GALACTOSE; MONOSACCHARIDE; RHAMNULOSE; TAGATOSE; UNCLASSIFIED DRUG; XYLULOSE;

ACETYLATION; AMINOLYSIS; ARTICLE; METHANOLYSIS; PRIORITY JOURNAL;

EID: 65549099058     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2009.03.016     Document Type: Article

References (31)

1. Brehm M., Göckel V.H., Jarglis P., and Lichtenthaler F.W. Tetrahedron: Asymmetry 19 (2008) 358
2. Yamaji K., Pada Sarker K., Maruyama I., and Hizukuri S. Planta Med. 68 (2002) 16
3. See extensive patent literature cited in:. Dekany G., Lundt I., Niedermair F., Bichler S., Spreitz J., Sprenger F.K., and Stütz A.E. Carbohydr. Res. 342 (2007) 1249
4. Ahrén B., Holst J.J., and Yu S. Eur. J. Pharmacol. 397 (2000) 219
5. Nakamura T., Nato A., Takahashi Y., and Akanuma H. J. Biochem. 99 (1986) 607
6. Baute A., Baute R., and Deffieux G. Phytochemistry 27 (1988) 3401
7. Taguchi T., Haruna M., and Okuda J. J. Biotechnol. Appl. Biochem. 18 (1993) 275
8. Yu S., Kenne M., and Pedersén M. Biochim. Biophys. Acta 1244 (1995) 1
9. Freimund S., Huwig A., Giffhorn F., and Köpper S. Chem. Eur. J. 4 (1998) 2442
10. Fujisue M., Yoshinaga K., Muroya K., Abe J., and Hizukuri S. J. Appl. Glycosci. 46 (1999) 439;
11. Barili P.L., Berti G., Catalani G., D'Andrea F., and Miarelli L. Carbohydr. Res. 274 (1995) 197
12. Freimund S., and Köpper S. Carbohydr. Res. 308 (1998) 195
13. Lichtenthaler F.W., and Metz T. Eur. J. Org. Chem. (2003) 3081
14. Lichtenthaler F.W., Jarglis P., and Hempe W. Liebigs Ann. Chem. (1983) 1959
15. For a detailed mechanistic discussion of γ-pyrone formation from hexoses, see:. Lichtenthaler F.W. Pure Appl. Chem. 50 (1978) 1357
16. Shah R.H., and Bahl O.P. Carbohydr. Res. 74 (1979) 105
17. Haga M., and Tejima S. Carbohydr. Res. 34 (1974) 214
18. Plötner A., and Maurer K. Ber. Dtsch. Chem. Ges. 64 (1931) 281
19. Lichtenthaler F.W., Kaji E., and Weprek S. J. Org. Chem. 50 (1985) 3505
20. Lemieux R.U., Nagabhushan T.L., and Gunner S.W. Can. J. Chem. 46 (1968) 405
21. Lemieux R.L., Earl R.A., James K., and Nagabhushan T.L. Can. J. Chem. 51 (1973) 19
22. Smiatacz Z., Myszka H., and Ciunik Z. Carbohydr. Res. 172 (1988) 171
23. Ciunik, Z.; Paulsen, H.; Luger, P.; Smiatacz, Z.; Myszka, H. Acta Crystallogr., Sect. B 1989, 45, 512
24. Ciunik Z., Szweda R., and Smiatacz Z. Carbohydr. Res. 219 (1991) 9
25. Hawkes G.E., Herwig K., and Roberts J.D. J. Org. Chem. 39 (1974) 1017
26. Kaiser M., Freiberg W., and Michalik M. J. Prakt. Chem. 338 (1996) 182
27. Maurer K., and Mahn H. Ber. Dtsch. Chem. Ges. 60 (1927) 1316
28. Maurer K., and Müller A. J. Org. Chem. 63 (1930) 2069
29. Ferrier R.J., and Sankey G.H. J. Chem. Soc. (C) (1966) 2339
30. Andersen S.M., Lundt I., Marcussen J., Søtofte L., and Yu S. Carbohydr. Res. 17 (1998) 1027
31. Lichtenthaler F.W., Liöhe A., and Cuny E. Liebigs Ann. Chem. (1983) 1973