Navegar

Colección

Datos Estadísticas

Artículo

Estamos trabajando para incorporar este artículo al repositorio
Consulte el artículo en la página del editor
Consulte la política de Acceso Abierto del editor

Abstract:

Purpurosamine C (1) is a component of the aminoglycoside antibiotic gentamicin C(1a). A derivative of 1 was synthesized from D-galactose via its 2-acetoxy-3,4,6-tri-O-acetyl glycal (3). Compound 3 undergoes glycosylation with 2-propanol in the presence of SnCl4, with two successive allylic rearrangements of the double bond to give isopropyl 6-O-acetyl-3,4-dideoxy- α-D-glycero-hex-3-enopyranosid-2-ulose (7). Compound 7 was hydrogenated, and O-deacetylated to afford 8. The free OH group of 8 was tosylated and substituted by azide, and the carbonyl function of the resulting ulose 10 reacted with hydroxylamine to give the E,Z-oximes (11,12). Highly diastereoselective reduction of the oxime acetate (13) by borane, which also reduced the azide function, led to the purpurosamine C derivative 14 (~40% yield from 3).

Registro:

Documento: Artículo
Título:Straightforward synthesis of a derivative of purpurosamine C from D- galactose
Autor:Zunszain, P.A.; Varela, O.
Filiación:CIHIDECAR (CONICET), Universidad de Buenos Aires, Ciudad Universitaria, Pabellón 2, 1428 Buenos Aires, Argentina
Palabras clave:galactose; gentamicin C; kanamycin derivative; purpurosamine c; unclassified drug; antibiotic therapy; article; chemical structure; conformational transition; deacetylation; drug synthesis; glycosylation; hydrogenation; priority journal; proton nuclear magnetic resonance; reduction; stereochemistry
Año:1998
Volumen:9
Número:7
Página de inicio:1269
Página de fin:1276
DOI: http://dx.doi.org/10.1016/S0957-4166(98)00083-4
Título revista:Tetrahedron Asymmetry
Título revista abreviado:Tetrahedron Asymmetry
ISSN:09574166
CODEN:TASYE
CAS:galactose, 26566-61-0, 50855-33-9, 59-23-4; gentamicin C, 11097-82-8, 25876-11-3, 26098-04-4
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_09574166_v9_n7_p1269_Zunszain

Referencias:

  • Umezawa, S., (1974) Adv. Carbohydr. Chem. Biochem., 30, p. 111
  • Kuwahara, R., Tsuchiya, T., (1997) Carbohydr. Res., 299, p. 271
  • Kondo, S., Iinuma, K., Yamamoto, H., Maeda, K., Umezawa, H., (1973) J. Antibiot., 26, p. 412
  • Guthrie, R.D., Williams, G.J., (1971) Chem. Commun., p. 923
  • Guthrie, R.D., Williams, G.J., (1972) J. Chem. Soc., Perkin Trans. 1, p. 2619
  • Cleophax, J., Leboul, J., Olesker, A., Gero, S.D., (1973) Tetrahedron Lett., p. 4911
  • Cleophax, J., Gero, S.D., Jegou-Aumont, E., Leboul, J., Mercier, D., (1975) J. Chem. Soc., Chem. Commun., p. 11
  • Brimacombe, J.S., Da'aboul, I., Tucker, L.C.N., (1975) J. Chem. Soc., Perkin Trans. 1, p. 979
  • Cleophax, J., Olesker, A., Rolland, A., Gero, S.D., Forchioni, A., (1977) Tetrahedron, 33, p. 1303
  • Brimacombe, J.S., Hunedy, F., Mather, A.M., Tucker, L.C.N., (1979) Carbohydr. Res., 68, p. 231
  • Ohashi, Y., Okuno, S., Takeda, K., Ito, Y., (1978) Carbohydr. Res., 67, p. 503
  • Liang, X., Krieger, R., Prinzbach, H., (1995) Tetrahedron Lett., 36, p. 6433
  • Brimacombe, J.S., Da'Aboul, I., Tucker, L.C.N., (1974) J. Chem. Soc., Perkin Trans. 1, p. 263
  • Golebiowski, A., Jacobsson, U., Chmielewski, M., Jurczak, J., (1987) Tetrahedron, 43, p. 599
  • Bauer, T., Jezewski, A., Jurczak, J., (1996) Tetrahedron: Asymmetry, 7, p. 1405
  • David, S., Lubineau, A., Gero, S.D., (1979) J. Org. Chem., 44, p. 4986
  • Varela, O., De Fina, G.M., De Lederkremer, R.M., (1988) Synthesis, p. 891
  • Varela, O., De Fina, G.M., De Lederkremer, R.M., (1987) Carbohydr. Res., 167, p. 187
  • Ferrier, R.J., (1969) Adv. Carbohydr. Chem. Biochem., 24, p. 199
  • Perlin, C.L., (1995) Tetrahedron, 51, p. 11901
  • Hawkes, G.E., Herwig, K., Roberts, J.D., (1974) J. Org. Chem., 39, p. 1017
  • Feuer, H., Braunstein, D.M., (1969) J. Org. Chem., 34, p. 1817
  • Hassner, A., Catsoulacos, P., (1967) Chem. Commun., p. 590
  • Danishefsky, S.J., Maring, C.H., (1985) J. Am. Chem. Soc., 107, p. 1269
  • Hassner, A., Levy, L.A., (1965) J. Am. Chem. Soc., 87, p. 4203
  • De Fina, G., Varela, O., De Lederkremer, R.M., (1993) Carbohydr. Res., 246, p. 1993

Citas:

---------- APA ----------
Zunszain, P.A. & Varela, O. (1998) . Straightforward synthesis of a derivative of purpurosamine C from D- galactose. Tetrahedron Asymmetry, 9(7), 1269-1276.
http://dx.doi.org/10.1016/S0957-4166(98)00083-4
---------- CHICAGO ----------
Zunszain, P.A., Varela, O. "Straightforward synthesis of a derivative of purpurosamine C from D- galactose" . Tetrahedron Asymmetry 9, no. 7 (1998) : 1269-1276.
http://dx.doi.org/10.1016/S0957-4166(98)00083-4
---------- MLA ----------
Zunszain, P.A., Varela, O. "Straightforward synthesis of a derivative of purpurosamine C from D- galactose" . Tetrahedron Asymmetry, vol. 9, no. 7, 1998, pp. 1269-1276.
http://dx.doi.org/10.1016/S0957-4166(98)00083-4
---------- VANCOUVER ----------
Zunszain, P.A., Varela, O. Straightforward synthesis of a derivative of purpurosamine C from D- galactose. Tetrahedron Asymmetry. 1998;9(7):1269-1276.
http://dx.doi.org/10.1016/S0957-4166(98)00083-4