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Abstract:

A tri-unsaturated derivative, i. e. 3-benzoyloxy-5-(3-benzoyloxy-allylldene)-(5H)-furan-2-one (5), previously described as 3-benzoyloxy-5-(2-benzoyloxyallylidene)-(5H)-furan-2-one (3), was obtained from cper-O-benzoyl-D-Cglycero-D-Cgulo-heptono-1,4-lactone via β-elimination in basic conditions. Stereoespecific catalytic hydrogenation rendered 2,7-di-O-benzoyl-3,5,6-trideoxy-(DL)-threo-heptono-1,4-lactone (6). Structures 5 and 6 were assigned on the basis of spectral studies. © 1984.

Registro:

Documento: Artículo
Título:β-Elimination in aldonolactones. Structure of the furan-2-one derivative obtained by benzoylation of D-glycero-D-gulo-heptono-1,4-lactone
Autor:Jeroncic, L.O.; Varela, O.J.; Fernandez Cirelli, A.; De Lederkremer, R.M.
Filiación:Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Ciudad Universitaria, 1428 Buenos Aires, Argentina
Año:1984
Volumen:40
Número:8
Página de inicio:1425
Página de fin:1430
DOI: http://dx.doi.org/10.1016/S0040-4020(01)82428-5
Título revista:Tetrahedron
Título revista abreviado:Tetrahedron
ISSN:00404020
CODEN:TETRA
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00404020_v40_n8_p1425_Jeroncic

Referencias:

  • de Lederkremer, Litter, (1971) Carbohydr. Res., 20, p. 442
  • Litter, de Lederkremer, (1973) Carbohydr. Res., 26, p. 431
  • Litter, de Lederkremer, (1974) Anales Asoc. Quím. Argentina, 62, p. 147
  • Varela, Fernández Cirelli, de Lederkremer, (1982) Carbohydr. Res., 100, p. 424
  • Kohn, Samaritano, Lerner, (1966) J. Org. Chem., 31, p. 1503
  • Fernández Cirelll, Sznaidman, Varela, de Lederkremer, (1983) Tetrahedron, 39, p. 313
  • Sala, Fernández Cirelli, de Lederkremer, (1980) Carbohydr. Res., 78, p. 61
  • Varela, Fernández Cirelli, de Lederkremer, (1980) Carbohydrate Research, 81, p. 130
  • Slessor, Tracey, (1971) Canadian Journal of Chemistry, 49, p. 2874
  • Hall, Black, Slessor, Tracey, (1972) Canadian Journal of Chemistry, 50, p. 1912
  • Slessor, Tracey, (1997) Carbohydr. Res., 27, p. 407

Citas:

---------- APA ----------
Jeroncic, L.O., Varela, O.J., Fernandez Cirelli, A. & De Lederkremer, R.M. (1984) . β-Elimination in aldonolactones. Structure of the furan-2-one derivative obtained by benzoylation of D-glycero-D-gulo-heptono-1,4-lactone. Tetrahedron, 40(8), 1425-1430.
http://dx.doi.org/10.1016/S0040-4020(01)82428-5
---------- CHICAGO ----------
Jeroncic, L.O., Varela, O.J., Fernandez Cirelli, A., De Lederkremer, R.M. "β-Elimination in aldonolactones. Structure of the furan-2-one derivative obtained by benzoylation of D-glycero-D-gulo-heptono-1,4-lactone" . Tetrahedron 40, no. 8 (1984) : 1425-1430.
http://dx.doi.org/10.1016/S0040-4020(01)82428-5
---------- MLA ----------
Jeroncic, L.O., Varela, O.J., Fernandez Cirelli, A., De Lederkremer, R.M. "β-Elimination in aldonolactones. Structure of the furan-2-one derivative obtained by benzoylation of D-glycero-D-gulo-heptono-1,4-lactone" . Tetrahedron, vol. 40, no. 8, 1984, pp. 1425-1430.
http://dx.doi.org/10.1016/S0040-4020(01)82428-5
---------- VANCOUVER ----------
Jeroncic, L.O., Varela, O.J., Fernandez Cirelli, A., De Lederkremer, R.M. β-Elimination in aldonolactones. Structure of the furan-2-one derivative obtained by benzoylation of D-glycero-D-gulo-heptono-1,4-lactone. Tetrahedron. 1984;40(8):1425-1430.
http://dx.doi.org/10.1016/S0040-4020(01)82428-5