Neighboring-group participation in benzylidene acetal ring-opening of a 2-cyano-2-deoxypyranoside derivative by diethylaluminum cyanide

Carbohydrate Research

Volumn 338, Issue 21, 2003, Pages 2177-2183

  Mangione, María I ^a   Suárez, Alejandra G ^a   Spanevello, Rolando A ^a  

^a Universidad Nacional de Rosario   (Argentina)

Author keywords

2 Cyano 2 deoxypyranoside; Benzylidene acetal; Diethylaluminum cyanide

Indexed keywords

AROMATIC COMPOUNDS; DERIVATIVES; MIXTURES; REACTION KINETICS; RING OPENING POLYMERIZATION;

CHEMICAL BEHAVIOR; RING OPENING REACTIONS;

SUGARS;

ACETAL DERIVATIVE; ALUMINUM DERIVATIVE; BENZYLIDENE DERIVATIVE; CYANIDE; CYANOHYDRIN; DIETHYLALUMINUM CYANIDE; ETHYLENE OXIDE; FUNCTIONAL GROUP; METHYL 2,3 ANHYDRO 4,6 O BENZYLIDENE ALPHA DEXTRO ALLOPYRANOSIDE; NITRILE; PYRANOSIDE; SUGAR; UNCLASSIFIED DRUG;

ARTICLE; METHODOLOGY; PRIORITY JOURNAL; REACTION ANALYSIS; RING OPENING;

BENZYLIDENE COMPOUNDS; GLYCOSIDES; MOLECULAR CONFORMATION; ORGANOMETALLIC COMPOUNDS; PYRANS;

EID: 1542399585     PISSN: 00086215     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0008-6215(03)00377-X     Document Type: Article

References (31)

1. Hall R.H., Bischofberger K., Brink A.J., de Villierrs O.G., Jordaan A. J. Chem. Soc., Perkin Trans. 1. 1979;781-786.
2. Mubarak A., Fraser-Reid B. J. Org. Chem. 47:1980;4265-4268.
3. Thang T.T., Winternitz F., Lagraange A., Olesker A., Lukacs G. Tetrahedron Lett. 21:1980;4495-4498.
4. Knierzinger A., Vasella A. J. Chem. Soc., Chem. Commun. 26:1984;9-11.
5. Pellegrinet S.C., Spanevello R.A. Tetrahedron: Asymmetry. 8:1997;1983-1986.
6. Pellegrinet S.C., Spanevello R.A. Tetrahedron Lett. 38:1997;8623-8626.
7. Poonian M.S., Nowoswiat E.F. J. Org. Chem. 45:1980;203-208.
8. Yang C.O., Wu H.Y., Fraser-Smith E.B. Tetrahedron Lett. 33:1992;37-40.
9. Azuma A., Nakajima Y., Nishizono N., Minakawa N., Suzuki M., Hanaoka K., Kobayashi T., Tanaka M., Sasaki T., Matsuda A. J. Med. Chem. 35:1993;4183-4189.
10. Collins P., Ferrier R. Monosaccharides. Their Chemistry and their Roles in Natural Products. 1995;280-289 J. Wiley & Sons, Chichester.
11. Hanessian, S. Total Synthesis of Natural Products: The Chiron Approach, Pergamon Press, Oxford, 1983, pp. 89, 125, 144, 265.
12. Williams N.R. J. Chem. Soc., Chem. Commun. 1967;1012-1013.
13. Inch T.D., Lewis G.J. Carbohydr. Res. 15:1970;1-10.
14. Sepulchre A.-M., Lukacs G., Vass G., Gero S.D. Angew. Chem., Int. Ed. 11:1972;148.
15. López J.C., Lameignére E., Burnouf C., Laborde M.A., Ghini A.A., Olesker A., Lukacs G. Tetrahedron. 49:1993;7701-7722.
16. Kazmi S.N-H., Ahmed Z., Khan A.Q., Malik A. Synth. Commun. 18:1988;151-156.
17. Davidson B.E., Guthrie R.D., McPhail A.T. J. Chem. Soc., Chem. Commun. 1968;1273-1274.
18. Davidson B.E., Guthrie R.D. J. Chem. Soc., Perkin Trans. 1. 1972;658-663.
19. Spanevello R.A., Pellegrinet S.C. Synth. Commun. 25:1995;3663-3670.
20. Watanabe S., Kavai I., Bobek M. J. Carbohydr. Chem. 14:1995;685-701.
21. Eliel E.L., Wilen S.H. Stereochemistry of Organic Compounds. 1994;730-731 J. Wiley & Sons, New York.
22. Wiggins L.F. Methods Carbohydr. Chem. 2:1963;188-191.
23. De las Heras F., San Felix A., Calvo-Mateo A., Fernandez-Resa P. Tetrahedron. 41:1985;3867-3873.
24. Inghardt T., Fredj T., Magnusson G. J. Org. Chem. 53:1988;4542-4548.
25. Kessler H., Griesinger J., Zarbock H.R., Loosli J. J. Magn. Res. 57:1984;331-335.
26. Olsson R., Berg U., Frejd T. Tetrahedron Lett. 38:1997;5701-5704.
27. Nagata W., Yoshioka M., Okumura T. J. Chem. Soc. (C). 1970;2365-2377.
28. Inghardt T., Frejd T. J. Org. Chem. 54:1989;5539-5543.
29. Olsson, R.; Berg, U.; Frejd, T. Tetrahedron 1998, 54, 3935-3954; idem 1998, 54, 5424.
30. Olsson, R.; Berg, U.; Frejd, T. Tetrahedron 1998, 54, 3935-3954; idem 1998, 54, 5424.
31. Davis F.A., Portonovo P.S., Reddy R.E., Chiu Y. J. Org. Chem. 61:1996;440-441.