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Abstract:

Methyl β-d-galactofuranoside (3) was readily obtained by tin(IV) chloridecatalyzed glycosylation of penta-O-benzoyl-α,β-d-galactofuranose (1), followed by debenzoylation with sodium methoxide. Glycosylation of 1 with 2,3,5-tri-O-benzoyl-d-galactono-1,4-lactone (4) or with the 6-O-trityl-lactone derivative 5 gave the benzoylated β-d-galactofuranosyl-(1→6)-d-galactono-1,4-lactone 6 in excellent yield. The structure of disaccharide 6 was confirmed by borohydride reduction to the glycosyl-alditol 7. A byproduct of the condensation reaction of 1 with 4 or 5 was identified as the benzoylated (1→1)-β,β′-d-galactofuranosyl disaccharide 8. Compound 8 was readily prepared (88% yield) by controlled addition of water to 1, in the presence of stannic chloride. O-Debenzoylation of 8 afforded crystalline β′-d-galactofuranosyl-(1→1)-β-d-galactofuranoside (9). The glycosyl-lactone 6 constitutes a key intermediate for the synthesis of a disaccharide derivative having both units in the furanoid form. Thus, diisoamylborane reduction of the lactone function of 6 led to the disaccharide derivative 10, from which the methyl glycoside 12 was prepared. O-Debenzoylation of 12 gave the corresponding methyl β-d-galactofuranosyl-(1→6)-β-d-galactofuranoside (13). The free disaccharide β-d-Galf-(1→6)-d-Galp (14) and its acetylated derivative (15) were also synthesized from 10. © 1989.

Registro:

Documento: Artículo
Título:Synthesis of galactofuranose disaccharides of biological significance
Autor:Marino, C.; Varela, O.; de Lederkremer, R.M.
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:disaccharide; galactose; galactoside; glycoside; article; chemical structure; chemistry; comparative study; conformation; glycosylation; Mycobacterium leprae; Mycobacterium tuberculosis; Mycoplasma mycoides; nuclear magnetic resonance spectroscopy; oxidation reduction reaction; synthesis; Carbohydrate Conformation; Chemistry; Comparative Study; Disaccharides; Galactose; Galactosides; Glycosides; Glycosylation; Magnetic Resonance Spectroscopy; Molecular Structure; Mycobacterium leprae; Mycobacterium tuberculosis; Mycoplasma mycoides; Oxidation-Reduction; Support, Non-U.S. Gov't
Año:1989
Volumen:190
Número:1
Página de inicio:65
Página de fin:76
DOI: http://dx.doi.org/10.1016/0008-6215(89)84147-3
Título revista:Carbohydrate Research
Título revista abreviado:Carbohydr. Res.
ISSN:00086215
CODEN:CRBRA
CAS:galactose, 26566-61-0, 50855-33-9, 59-23-4; Disaccharides; Galactose, 26566-61-0; Galactosides; Glycosides
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00086215_v190_n1_p65_Marino

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Citas:

---------- APA ----------
Marino, C., Varela, O. & de Lederkremer, R.M. (1989) . Synthesis of galactofuranose disaccharides of biological significance. Carbohydrate Research, 190(1), 65-76.
http://dx.doi.org/10.1016/0008-6215(89)84147-3
---------- CHICAGO ----------
Marino, C., Varela, O., de Lederkremer, R.M. "Synthesis of galactofuranose disaccharides of biological significance" . Carbohydrate Research 190, no. 1 (1989) : 65-76.
http://dx.doi.org/10.1016/0008-6215(89)84147-3
---------- MLA ----------
Marino, C., Varela, O., de Lederkremer, R.M. "Synthesis of galactofuranose disaccharides of biological significance" . Carbohydrate Research, vol. 190, no. 1, 1989, pp. 65-76.
http://dx.doi.org/10.1016/0008-6215(89)84147-3
---------- VANCOUVER ----------
Marino, C., Varela, O., de Lederkremer, R.M. Synthesis of galactofuranose disaccharides of biological significance. Carbohydr. Res. 1989;190(1):65-76.
http://dx.doi.org/10.1016/0008-6215(89)84147-3