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Abstract:

The lactonic disaccharide 2,3,5-tri-O-benzoyl-6-O-(2,3,4,6-tetra-O-acetyl-β-d-glucopyranosyl)-d-galactono-1,4-lactone (7) was prepared by condensing 6-O-trityl-2,3,5-tri-O-benzoyl-d-galactono-1,4-lactone (2) with 2,3,4,6-tetra-O-acetyl-α-d-glucopyranosyl bromide (4) or with 1,2,3,4,6-penta-O-acetyl-β-d-glucopyranose (6). The reaction was carried out using various catalysts. In the presence of silver trifluoromethanesulfonate or tin(IV) chloride, formation of the 1,2-trans glycosidic bond took place stereoselectively, to afford compound 7 in good yields. However, condensation of 2,3,5-tri-O-benzoyl-d-galactono-1,4-lactone (3) with 4 catalyzed by mercuric salts gave 3,4,6-tri-O-acetyl-1,2-O-[1(S)-(2,3,5-tri-O-benzoyl-d-galactono-1,4-lacton-6-yloxy)ethylidene]-α-d- glucopyranose (5) as the main product. Reduction of the lactone function of 7 with bis(3-methyl-2-butyl)borane led to 2,3,5-tri-O-benzoyl-6-O-(2,3,4,6-tetra-O-acetyl-β-d-glucopyranosyl)-β-d-galactofuranose (8). © 1989.

Registro:

Documento: Artículo
Título:A new approach to the synthesis of disaccharide derivatives having a furanose as the reducing unit
Autor:du Mortier, 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
Año:1989
Volumen:189
Número:C
Página de inicio:79
Página de fin:86
DOI: http://dx.doi.org/10.1016/0008-6215(89)84087-X
Título revista:Carbohydrate Research
Título revista abreviado:Carbohydr. Res.
ISSN:00086215
CODEN:CRBRA
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00086215_v189_nC_p79_duMortier

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Citas:

---------- APA ----------
du Mortier, C., Varela, O. & de Lederkremer, R.M. (1989) . A new approach to the synthesis of disaccharide derivatives having a furanose as the reducing unit. Carbohydrate Research, 189(C), 79-86.
http://dx.doi.org/10.1016/0008-6215(89)84087-X
---------- CHICAGO ----------
du Mortier, C., Varela, O., de Lederkremer, R.M. "A new approach to the synthesis of disaccharide derivatives having a furanose as the reducing unit" . Carbohydrate Research 189, no. C (1989) : 79-86.
http://dx.doi.org/10.1016/0008-6215(89)84087-X
---------- MLA ----------
du Mortier, C., Varela, O., de Lederkremer, R.M. "A new approach to the synthesis of disaccharide derivatives having a furanose as the reducing unit" . Carbohydrate Research, vol. 189, no. C, 1989, pp. 79-86.
http://dx.doi.org/10.1016/0008-6215(89)84087-X
---------- VANCOUVER ----------
du Mortier, C., Varela, O., de Lederkremer, R.M. A new approach to the synthesis of disaccharide derivatives having a furanose as the reducing unit. Carbohydr. Res. 1989;189(C):79-86.
http://dx.doi.org/10.1016/0008-6215(89)84087-X