Characterisation and X-ray crystallography of products from the Bucherer-Bergs reaction of methyl 2,3-O-isopropylidene-α -D-lyxo-pentodialdo-1,4-furanoside

Carbohydrate Research

Volumn 338, Issue 19, 2003, Pages 1917-1924

  Mičová, Júlia ^a   Steiner, Bohumil ^a   Koóš, Miroslav ^a   Langer, Vratislav ^b   Gyepesová, Dalma ^a  

^a INSTITUTE OF CHEMISTRY   (Slovakia)

^b CHALMERS UNIVERSITY OF TECHNOLOGY   (Sweden)

Author keywords

Bucherer Bergs reaction; Furanosiduronamide; Pentodialdo 1,4 furanoside; Pyrido 2,1 e imidazolidine; X ray crystallography

Indexed keywords

CONFORMATIONS; NUCLEAR MAGNETIC RESONANCE; X RAY CRYSTALLOGRAPHY;

MASS SPECTRAL DATAS;

ORGANIC COMPOUNDS;

5,6 DIHYDRO 6 HYDROXY 4,5 ISOPROPYLIDENEDIOXY 4H PYRIDO[2,1 E]IMIDAZOLIDINE 2',4' DIONE; FURAN DERIVATIVE; HYDANTOIN DERIVATIVE; METHYL 2,3 O ISOPROPYLIDENE ALPHA DEXTRO LYXOPENTODIALDO 1,4 FURANOSIDE; METHYL 2,3 O ISOPROPYLIDENE ALPHA DEXTRO MANNOFURANOSIDURONAMIDE; METHYL 2,3 O ISOPROPYLIDENE ALPHA DEXTRO MANNOFURANOSIDURONIC ACID; METHYL 2,3 O ISOPROPYLIDENE ALPHA DEXTRO MANNOFURANOSIDURONONITRILE; METHYL 5 DEOXY 2,3 O ISOPROPYLIDENE 5 UREIDO BETA LEVO GULOFURANOSIDURONAMIDE; UNCLASSIFIED DRUG;

ARTICLE; BUCHERER BERGS REACTION; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CONFORMATION; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; X RAY CRYSTALLOGRAPHY;

STAPHYLOCOCCUS PHAGE 3A;

EID: 0142026924     PISSN: 00086215     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0008-6215(03)00307-0     Document Type: Article

References (32)

1. Bucherer H.T., Fischbeck H.T. J. Prakt. Chem. 140:1934;69;
2. Bergs, H. Ger. pat. 566,094, 1929.
3. Hoyer H.L. Chem. Ber. 83:1950;491.
4. Ware E. Chem. Rev. 46:1950;422.
5. Yanagisawa H., Kinoshita M., Nakada S., Umezawa S. Bull. Chem. Soc. Jpn. 43:1970;246-252.
6. Rosenthal A., Dodd R.R. J. Carbohydr. Nucleos. Nucleot. 6:1979;467-476.
7. Kuszmann J., Márton-Merész M., Jerkovich G. Carbohydr. Res. 175:1988;249-264.
8. Lamberth C., Blarer S. Synlett. 1994;489-490.
9. Sano H., Sugai S. Tetrahedron. 51:1995;4635-4646.
10. Koóš M., Steiner B., Langer V., Gyepesová D., Ďurík M. Carbohydr. Res. 328:2000;115-126.
11. Koóš M., Steiner B., Mičová J., Langer V., Ďurík M., Gyepesová D. Carbohydr. Res. 332:2001;351-361.
12. Mičová J., Steiner B., Koóš M., Langer V., Gyepesová D. Synlett. 2002;1715-1717.
13. Steiner, B.; Mičová, J.; Koóš, M.; Langer, V.; Gyepesová, D. Carbohydr. Res., 2003, 338, 1349-1357.
14. Postel D., Nguyen Van Nhien A., Villa P., Ronco G. Tetrahedron Lett. 42:2001;1499-1502.
15. Haruyama H., Takayama T., Kinoshita T., Kondo M., Nakajima M., Haneishi T. J. Chem. Soc. Perkin Trans. 1. 1991;1637-1640.
16. Nakajima M., Itoi K., Takamatsu Y., Kinoshita T., Okazaki T., Kawakubo K., Shindo M., Honma T., Tohjigamori M., Haneishi T. J. Antibiot. 44:1991;293-300.
17. Nakajima N., Matsumoto M., Kirihara M., Hashimoto M., Katoh T., Terashima S. Tetrahedron. 52:1996;1177-1194.
18. Estevez J.C., Estevez R.J., Ardron H., Wormald M.R., Brown D., Fleet G.W.J. Tetrahedron Lett. 35:1994;8885-8888.
19. Estevez J.C., Smith M.D., Lane A.L., Crook S., Watkin D.J., Besra G.S., Brennan P.J., Nash R.J., Fleet G.W.J. Tetrahedron: Asymmetry. 7:1996;387-390.
20. Krajewski J.W., Gluzinski P., Pakulski Z., Zamojski A., Mishnev A., Kemme A. Carbohydr. Res. 252:1994;97-105.
21. Barton D.H.R., Gero S.D., Quiclet-Sire B., Samadi M. Tetrahedron: Asymmetry. 5:1994;2123-2136.
22. Mičová J., Steiner B., Koóš M., Gajdoš J., Langer V., Gyepesová D. Molecules. 7:2002;437-446.
23. Mičová J., Steiner B., Koóš M., Langer V., Ďurík M., Gyepesová D., Smrčok L. Carbohydr. Res. 337:2002;663-672.
24. Cremer D., Pople J.A. J. Am. Chem. Soc. 97:1975;1354-1358.
25. Bernstein J., Davis R.E., Shimoni L., Chang L.-N. Angew. Chem., Int. Ed. Engl. 34:1995;1555-1573.
26. Motherwell W.D.S., Shields G.P., Allen F.H. Acta Crystallogr., Sect. B. 55:1999;1044-1056.
27. Pätoprstý, V.; Kovácik, V.; Karácsonyi, Š. Rapid Commun. Mass Spectrom. 1995, 9, 840-844.
28. Siemens AXS. SMART & SAINT; Madison, WI, USA, 1995.
29. Sheldrick, G. M. Program SADABS; University of Göttingen: Germany, 2001.
30. Blessing R.H. Acta Crystallogr., Sect. A. 51:1995;33-38.
31. Bruker AXS Inc. SHELXTL Version 6.10; Madison, WI, USA, 2001.
32. Brandenburg, K. DIAMOND: Visual Crystal Structure Information System, Version 2.1d; Crystal Impact GbR: Bonn, Germany, 2000.