Preparation of 2,6-anhydro-aldose acylhydrazones, -semicarbazones and -oximes from 2,6-anhydro-aldononitriles (glycosyl cyanides)

Carbohydrate Research

Volumn 338, Issue 12, 2003, Pages 1319-1325

  Tóth, Marietta ^a   Somsák, László ^a  

^a UNIVERSITY OF DEBRECEN   (Hungary)

Author keywords

C Glycosyl compounds; Hydrazones; Oximes

Indexed keywords

CATALYSIS; CYANIDES; DERIVATIVES; MOLECULAR STRUCTURE; REDUCTION;

OXIMES; SEMICARBAZONES;

SUGARS;

ACID; AZO COMPOUND; CARBAZIC ACID DERIVATIVE; CYANIDE; GLYCOSIDE; HYDRAZINE DERIVATIVE; HYDRAZONE DERIVATIVE; HYDROXYLAMINE; NITRILE; OXIME; OXIME DERIVATIVE; PYRIDINE; SEMICARBAZONE DERIVATIVE; SOLVENT; THIOSEMICARBAZIDE; WATER;

ACYLATION; AMINATION; ARTICLE; CATALYSIS; CHEMICAL MODEL; CHEMICAL STRUCTURE; CHEMISTRY; COLUMN CHROMATOGRAPHY; CRYSTALLIZATION; GLYCOSYLATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; ROOM TEMPERATURE; SYNTHESIS;

EID: 0038697613     PISSN: 00086215     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0008-6215(03)00163-0     Document Type: Article

References (29)

1. Klamann, D.; Hagemann, H. (Eds.) Organische Stickstoff-Verbindungen mit einer C,N-Doppelbindung, Thieme: Stuttgart, 1990; Vol. E14b.
2. Tennant G. Imines, nitrones, nitriles, and isocyanides. Sutherland I.O. Comprehensive Organic Chemistry. 2:1979;385-443 Pergamon Press, Oxford.
3. Enders D., Reinhold U. Tetrahedron-Asymmetry. 8:1997;1895-1946.
4. Bloch R. Chem. Rev. 98:1998;1407-1438.
5. Steinig A.G., Spero D.M. Org. Prep. Proc. Int. 32:2000;205-234.
6. Ãbele E., Lukevics E. Org. Prep. Proc. Int. 32:2000;235-264.
7. Adams J.P. J. Chem. Soc., Perkin Trans. 1. 2000;125-139.
8. Friestad G.K. Tetrahedron. 57:2001;5461-5496.
9. Collins P.M., Ferrier R.J. Monosaccharides - Their Chemistry and Their Roles in Natural Products. 1995;112-115 John Wiley & Sons, Chichester.
10. For a collection of synthetic methods of anhydro-aldoses see a recent review: Somsák L. Chem. Rev. 101:2001;81-135. (Section III. C).
11. Kim S., Lee I.Y., Yoon J.-Y., Oh D.H. J. Am. Chem. Soc. 118:1996;5138-5139.
12. Pham-Huu D.-P., Petrušova M., BeMiller J.N., Petruš L. Synlett. 1998;1319-1320.
13. Pham-Huu D.-P., Petrušova M., BeMiller J.N., Petruš L. J. Carbohydr. Chem. 19:2000;93-110.
14. Baker K.W.J., Gibb A., March A.R., Paton R.M. Tetrahedron Lett. 42:2001;4065-4068.
15. Dondoni A., Junquera F., Merchan F.L., Merino P., Scherrmann M.C., Tejero T. J. Org. Chem. 62:1997;5484-5496.
16. Martin O.R., Khamis F.E., Rao S.P. Tetrahedron Lett. 30:1989;6143-6146.
17. Yamago S., Miyazoe H., Goto R., Hashidume M., Sawazaki T., Yoshida J. J. Am. Chem. Soc. 123:2001;3697-3705.
18. Kovács L., Osz E., Domokos V., Holzer W., Györgydeák Z. Tetrahedron. 57:2001;4609-4621.
19. Tóth M., Somsák L. Tetrahedron Lett. 42:2001;2723-2725.
20. Tóth M., Somsák L. J. Chem. Soc., Perkin. Trans. 1. 2001;942-943.
21. Tóth, M.; Kövér, K. E.; Bényei, A.; Somsák, L. manuscript in preparation.
22. Plieninger H., Werst G. Angew. Chem. 67:1955;156-157.
23. Plieninger H., Werst G. Chem. Ber. 88:1955;1956-1961.
24. Plieninger H., Kiefer B. Chem. Ber. 90:1957;617-623.
25. Rabinovitz M. Reduction of the cyano group. Rappoport Z. The Chemistry of the Cyano Group. 1970;307-340 John Wiley & Sons, London.
26. Albrecht H.P., Repke D.B., Moffatt J.G. J. Org. Chem. 38:1973;1836-1840.
27. Dettinger H.-M., Kurz G., Lehmann J. Carbohydr. Res. 74:1979;301-307.
28. Schmidt R.R., Frische K. Bioorg. Med. Chem. Lett. 8:1993;1747-1750.
29. Frische K., Schmidt R.R. Liebigs Ann. 1994;297-303.