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Abstract:

The key step in a new synthesis of 2-acetamido-2,3-dideoxy-(14)-thiodisaccharides was the conjugate addition of a 1-thiogalactose derivative to E and Z acetyl oximes derived from sugar enones. This reaction was shown to be completely diastereoselective for both the formation of the thioglycosidic linkage and the configuration of acetyl oxime. The thiodisaccharides have been designed as inhibitors of the β-galactosidase from E. coli, and they have been shown to successfully meet such requirements. © 2018 American Chemical Society.

Registro:

Documento: Artículo
Título:Design and Synthesis of 2-Acetamido-2,3-dideoxythiodisaccharides via Diastereoselective Conjugate Addition to Sugar Enone O-Acetyl Oximes. Galactosidase Inhibition Studies
Autor:Dada, L.; Manzano, V.E.; Varela, O.
Filiación:Universidad de Buenos Aires, Facultad de Ciencias Exactas y Naturales, Departamento de Química Orgánica, Ciudad Universitaria, Pabellón 2, Buenos Aires, C1428EHA, Argentina
CONICET-UBA, Centro de Investigación en Hidratos de Carbono (CIHIDECAR), Buenos Aires, C1425FQB, Argentina
Año:2018
Volumen:20
Número:19
Página de inicio:6225
Página de fin:6228
DOI: http://dx.doi.org/10.1021/acs.orglett.8b02692
Título revista:Organic Letters
Título revista abreviado:Org. Lett.
ISSN:15237060
CODEN:ORLEF
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_15237060_v20_n19_p6225_Dada

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Citas:

---------- APA ----------
Dada, L., Manzano, V.E. & Varela, O. (2018) . Design and Synthesis of 2-Acetamido-2,3-dideoxythiodisaccharides via Diastereoselective Conjugate Addition to Sugar Enone O-Acetyl Oximes. Galactosidase Inhibition Studies. Organic Letters, 20(19), 6225-6228.
http://dx.doi.org/10.1021/acs.orglett.8b02692
---------- CHICAGO ----------
Dada, L., Manzano, V.E., Varela, O. "Design and Synthesis of 2-Acetamido-2,3-dideoxythiodisaccharides via Diastereoselective Conjugate Addition to Sugar Enone O-Acetyl Oximes. Galactosidase Inhibition Studies" . Organic Letters 20, no. 19 (2018) : 6225-6228.
http://dx.doi.org/10.1021/acs.orglett.8b02692
---------- MLA ----------
Dada, L., Manzano, V.E., Varela, O. "Design and Synthesis of 2-Acetamido-2,3-dideoxythiodisaccharides via Diastereoselective Conjugate Addition to Sugar Enone O-Acetyl Oximes. Galactosidase Inhibition Studies" . Organic Letters, vol. 20, no. 19, 2018, pp. 6225-6228.
http://dx.doi.org/10.1021/acs.orglett.8b02692
---------- VANCOUVER ----------
Dada, L., Manzano, V.E., Varela, O. Design and Synthesis of 2-Acetamido-2,3-dideoxythiodisaccharides via Diastereoselective Conjugate Addition to Sugar Enone O-Acetyl Oximes. Galactosidase Inhibition Studies. Org. Lett. 2018;20(19):6225-6228.
http://dx.doi.org/10.1021/acs.orglett.8b02692