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Abstract:

Benzoylation of d-galactono-1,4-lactone with 2.2 mol of benzoyl chloride, at -23°, gave the 2,6-dibenzoate (2, 62%). Tin(IV) chloride-catalyzed glycosylation of 2 with 1,2,3,5,6-penta-O-benzoyl-α,β-d-galactofuranose (1) afforded 2,6-di-O-benzoyl-5-O-(2,3,5,6-tetra-O-benzoyl-β-d-galactofuranosyl)-d-galactono-1,4-lactone (4, 70%), HO-3 of which was benzoylated to give 5. The structure of 4 was confirmed by its conversion into crystalline β-d-Galf-(1→5)-d-Gal-ol (8). Reduction of the lactone function of 5 with di-isoamylborane followed by debenzoylation gave β-d-Galf-(1→5)-d-Galf (7). A by-product of the condensation of 1 with 2 was characterized as 2,6-di-O-benzoyl-3,5-di-O-(2,3,5,6-tetra-O-benzoyl-β-d-galactofuranosyl)-d-galactono-1,4-lactone (9), which was converted, as for 5, into β-d-Galf-(1→3)[β-d-Galf-(1→5)]-d-Galf (13). © 1990.

Registro:

Documento: Artículo
Título:Convenient syntheses of 5-O- and 3,5-di-O-(β-d-galactofuranosyl)-d-galactofuranose
Autor:de Lederkremer, R.M.; Marino, C.; Varela, O.
Filiación:Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Ciudad Universitaria, Pabellon II, 1428 Buenos Aires, Argentina
Palabras clave:3,5 di O (beta galactofuranosyl) galactofuranose; 3,5-di-O-(beta-galactofuranosyl)-galactofuranose; 5 O beta galactofuranosyl galactofuranose; 5-O-beta-galactofuranosyl-galactofuranose; disaccharide; trisaccharide; article; carbohydrate analysis; chemistry; molecular genetics; synthesis; Carbohydrate Sequence; Chemistry; Disaccharides; Molecular Sequence Data; Support, Non-U.S. Gov't; Trisaccharides
Año:1990
Volumen:200
Número:C
Página de inicio:227
Página de fin:235
DOI: http://dx.doi.org/10.1016/0008-6215(90)84193-X
Título revista:Carbohydrate Research
Título revista abreviado:Carbohydr. Res.
ISSN:00086215
CODEN:CRBRA
CAS:3,5-di-O-(beta-galactofuranosyl)-galactofuranose, 129728-10-5; 5-O-beta-galactofuranosyl-galactofuranose, 129728-07-0; Disaccharides; Trisaccharides
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00086215_v200_nC_p227_deLederkremer

Referencias:

  • McNeill, Wallner, Hunter, Brennan, (1987) Carbohydr. Res., 166, pp. 299-308
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  • Sugawara, Nakayama, Ogawa, Synthetic studies on glycosidic phytotoxins. Part III. Synthetic studies on derivatives of 5-O-.BETA.-D-galactofuranosyl-D-galactofuranose. (1986) Agricultural and Biological Chemistry, 50, pp. 1557-1561

Citas:

---------- APA ----------
de Lederkremer, R.M., Marino, C. & Varela, O. (1990) . Convenient syntheses of 5-O- and 3,5-di-O-(β-d-galactofuranosyl)-d-galactofuranose. Carbohydrate Research, 200(C), 227-235.
http://dx.doi.org/10.1016/0008-6215(90)84193-X
---------- CHICAGO ----------
de Lederkremer, R.M., Marino, C., Varela, O. "Convenient syntheses of 5-O- and 3,5-di-O-(β-d-galactofuranosyl)-d-galactofuranose" . Carbohydrate Research 200, no. C (1990) : 227-235.
http://dx.doi.org/10.1016/0008-6215(90)84193-X
---------- MLA ----------
de Lederkremer, R.M., Marino, C., Varela, O. "Convenient syntheses of 5-O- and 3,5-di-O-(β-d-galactofuranosyl)-d-galactofuranose" . Carbohydrate Research, vol. 200, no. C, 1990, pp. 227-235.
http://dx.doi.org/10.1016/0008-6215(90)84193-X
---------- VANCOUVER ----------
de Lederkremer, R.M., Marino, C., Varela, O. Convenient syntheses of 5-O- and 3,5-di-O-(β-d-galactofuranosyl)-d-galactofuranose. Carbohydr. Res. 1990;200(C):227-235.
http://dx.doi.org/10.1016/0008-6215(90)84193-X