Synthesis of 4-carbamoyl-2-oxazolidinones C-4-linked with a saccharide moiety via Bucherer-Bergs reaction of hexofuranos-5-uloses

Synlett

Volumn , Issue 10, 2002, Pages 1715-1717

  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

5 hexofuranos 5 uloses; 5 membered heterocycles; Bucherer Bergs reaction; Carbohydrates; Conjugation

Indexed keywords

4 CARBAMOYL 2 OXAZOLIDINONE DERIVATIVE; 5 HEXOFURANOS 5 ULOSE; CARBOHYDRATE; CARBOHYDRATE DERIVATIVE; CARBON; HYDANTOIN DERIVATIVE; OXAZOLIDINONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CRYSTAL STRUCTURE; HYDROLYSIS; ISOMERISM; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STEREOCHEMISTRY; SYNTHESIS;

EID: 0036400028     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2002-34222     Document Type: Article

References (14)

1. Koóš, M.; Steiner, B.; Mičová, J.; Langer, V.; Ďurík, M.; Gyepesová, D. Carbohydr. Res. 2001, 332, 351.
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6. 13C NMR and mass spectral data and at present, they are subjected to X-ray analysis to determine the configuration at C-5.
7. Bucherer, H. T.; Lieb, V. A. J. Prakt. Chem. 1934, 141, 5.
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10. Theobald, R. S. In Rodd's Chemistry of Carbon Compounds, 2nd ed., Vol. IV C; Ansell, M. F., Ed.; Elsevier: Amsterdam, 1986, 119.
11. Koóš, M.; Steiner, B.; Langer, V.; Gyepesová, D.; Ďurík, M. Carbohydr. Res. 2000, 328, 115.
12. 7: C, 47.70; H, 6.00; N, 9.27. Found: C, 47.81; H, 6.08; N, 9.20. The 2-oxazolidinone derivatives 7-10 were prepared analogously (yield: 7, 38%; 8, 45%; 9, 41%; 10, 44%), starting from the corresponding 5-uloses.
13. Pätoprstý, V.; Kováčik, V.; Karácsonyi, Š, Rapid Commun. Mass Spectrom. 1995, 9, 840.
14. Crystallographic data for 4 has been deposited with the Cambridge Crystallographic Data Centre, CCDC No. 178704. Copies of this information may be obtained free of charge from The Director, CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (Fax: +44(1223)336033; e-mail: deposit@ccdc.cam.ac.uk).