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Abstract:

The synthesis of pyranoid and furanoid derivatives of 6-deoxy-4-thio-D-galactose from methyl α-D-glucopyranoside (1) is described. A key intermediate for the synthesis, methyl 2,3-di-O-benzoyl-6-deoxy-4-thio-α-D-galactopyranoside (15) was prepared by different approaches from 1. Regioselectivity for the protection or modification of the hydroxyl groups of 1 or its derivatives was achieved by employing various reagents. The thiol group at C-4 was introduced by nucleophilic substitution of a tosylate by thiocyanate followed by reduction or alkaline methanolysis of the thiocyano group. A by-product of the latter reaction was characterized as a monothiolcarbonate derivative (17), whose conformation was studied by molecular mechanics calculations. Acetolysis of methyl 6-deoxy-4-thio-α-D-galactopyranoside (16) afforded ring sulfur containing derivatives of 6-deoxy-4-thio-D-galactofuranose, which are described for the first time. © 1990.

Registro:

Documento: Artículo
Título:Synthesis of furanoid and pyranoid derivatives of 6-deoxy-4-thio-D-galactose
Autor:Cicero, D.; 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:1990
Volumen:46
Número:4
Página de inicio:1131
Página de fin:1144
DOI: http://dx.doi.org/10.1016/S0040-4020(01)86679-5
Título revista:Tetrahedron
Título revista abreviado:Tetrahedron
ISSN:00404020
CODEN:TETRA
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00404020_v46_n4_p1131_Cicero

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Citas:

---------- APA ----------
Cicero, D., Varela, O. & De Lederkremer, R.M. (1990) . Synthesis of furanoid and pyranoid derivatives of 6-deoxy-4-thio-D-galactose. Tetrahedron, 46(4), 1131-1144.
http://dx.doi.org/10.1016/S0040-4020(01)86679-5
---------- CHICAGO ----------
Cicero, D., Varela, O., De Lederkremer, R.M. "Synthesis of furanoid and pyranoid derivatives of 6-deoxy-4-thio-D-galactose" . Tetrahedron 46, no. 4 (1990) : 1131-1144.
http://dx.doi.org/10.1016/S0040-4020(01)86679-5
---------- MLA ----------
Cicero, D., Varela, O., De Lederkremer, R.M. "Synthesis of furanoid and pyranoid derivatives of 6-deoxy-4-thio-D-galactose" . Tetrahedron, vol. 46, no. 4, 1990, pp. 1131-1144.
http://dx.doi.org/10.1016/S0040-4020(01)86679-5
---------- VANCOUVER ----------
Cicero, D., Varela, O., De Lederkremer, R.M. Synthesis of furanoid and pyranoid derivatives of 6-deoxy-4-thio-D-galactose. Tetrahedron. 1990;46(4):1131-1144.
http://dx.doi.org/10.1016/S0040-4020(01)86679-5