Methyl D-arabino-hex-2-ulopyranosonate as a building block for spiro[1,4-benzoxazine-2,2'-pyrans]

Carbohydrate Research

Volumn 316, Issue 1-4, 1999, Pages 85-94

  Andersch, Jens ^a   Sicker, Dieter ^a   Wilde, Horst ^a  

^a UNIVERSITY OF LEIPZIG   (Germany)

Author keywords

Cyclic hydroxamic acid; D arabino Hex 2 ulopyranosonates; Glycosidation; Spiro 1,4 benzoxazine 2,2' pyran ones

Indexed keywords

BENZOXAZINE DERIVATIVE; HYDROXAMIC ACID DERIVATIVE; SPIRO COMPOUND;

ARTICLE; CARBOHYDRATE ANALYSIS; CARBOHYDRATE SYNTHESIS; CHEMICAL MODIFICATION; CYCLIZATION; HYDROGENATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; REACTION ANALYSIS;

EID: 0032995019     PISSN: 00086215     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0008-6215(99)00039-7     Document Type: Article

References (27)

1. Lichtenthaler F.W. Carbohydrates as Organic Raw Materials. 1990;VCH, Weinheim.
2. Bols M. Carbohydrate Building Blocks. 1996;Wiley, New York.
3. P. Fahrni, T. Siegfried, Eur. Patent EP 133 493 (1985); Chem. Abstr., 103 (1985), 178578c.
4. (a) W.N. Haworth, E.L. Hirst, J. Chem. Soc., (1926) 1858-1868.
5. (b) W.N. Haworth, E.L. Hirst, A. Learner, J. Chem. Soc., (1927) 1040-1049.
6. (c) C.G. Anderson, W. Charlton, W.N. Haworth, V.S. Nicholson, J. Chem. Soc., (1929) 1337-1346.
7. (d) M.L. Wolfrom, W.W. Binkley, W.L. Shilling, H.W. Hilton, J. Am. Chem. Soc., 73 (1951) 3553-3557.
8. (a) M. Bobek, J. Farkas, F. Sorm, Collect. Czech. Chem. Commun., 32 (1967) 3572-3580.
9. (b) H. Ohle, Ber. Dtsch. Chem. Ges., 67 (1934) 155-162.
10. Geigert J., Neidleman S.L., Hirano D.S., Wolf B., Panschar B.M. Carbohydr. Res. 113:1983;163-165.
11. Bouvet O.M.M., Lenormand P., Grimont P.A.D. Int. J. Syst. Bacteriol. 39:1989;61-67.
12. Kirrbach S., Schnelle R.-R., Hauptmann S., Mann G., Wilde H., Sicker D., Stottmeister U. J. Prakt. Chem. 334:1992;537-539.
13. Crawford T.C., Andrews G.C., Faubl H., Chmurny G.N. J. Am. Chem. Soc. 102:1980;2220-2225.
14. Sicker D., Hartenstein H., Kluge M. Natural benzoxazinoids - Synthesis of acetal glucosides, aglucones, analogues. Pandalai S.G. Recent Research Developments in Phytochemistry. 1:1997;203-223 Research Signpost, Trivandrum, India.
15. Kluge M., Grambow H.J., Sicker D. Phytochemistry. 44:1997;639-641.
16. Wolf R.B., Spencer G.F., Plattner R.D. J. Nat. Prod. 48:1985;59-63.
17. Özden S., Özden T., Attila J., Kücükislamoglu M., Okatan A. J. Chromatogr. 609:1992;402-406.
18. Pratt K., Kumar P., Chilton W.S. Biochem. Syst. Ecol. 23:1995;781-785.
19. Kluge M., Sicker D. Tetrahedron. 52:1996;10389-10398.
20. Kluge M., Schneider B., Sicker D. Carbohydr. Res. 298:1997;147-152.
21. Ohle H., Wolter R. Ber. Dtsch. Chem. Ges. 63:1930;843-852.
22. Major M., Cook W.J. J. Am. Chem. Soc. 58:1936;2477-2478.
23. Hartenstein H., Sicker D. J. Prakt. Chem. 335:1993;359-362.
24. L. Somsák, I. Bajaza, L. Kossuth, Liebigs Ann. Chem., (1990) 1265-1268.
25. J. Andersch, PhD thesis, Fakultät für Chemie und Mineralogie der Universität Leipzig, 1998.
26. Lehmann J. Kohlenhydrate. 1996;49-54 Georg Thieme Verlag, Stuttgart.
27. P. Köll, E. Steinweg, J. Metzger, B. Meyer, Liebigs Ann. Chem. (1982) 1052-1062.