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Abstract:

Methyl 2,3-di-O-benzoyl-6-deoxy-4-O-(p-tolylsulfonyl) and 4-O-[(p-nitrophenyl)sulfonyl]-α-d-mannopyranosides (9 and 10) were prepared by three different routes from methyl α-d-mannopyranoside (1). The analogous 4-sulfonyloxy derivatives having HO-2 and HO-3 free (14 and 15) were also synthesized from 1. Nucleophilic substitution of the sulfonyloxy group of 9, 10, 14, and 15 by potassium thiocyanate in N,N-dimethylformamide was attempted. Compounds 9 and 10 gave a mixture of solvolysis products: methyl 2,3-di-O-benzoyl-6-deoxy-α-d-talopyranoside (17), methyl 3,4-di-O-benzoyl-6-deoxy-α-d-talopyranoside (18), and methyl 2,4-di-O-benzoyl-6-deoxy-α-d-talopyranoside (19), which are evidently formed by intramolecular displacement of the 4-sulfonate by backside attack of the C-2 benzoyloxy substituent, followed by benzoyl migration. The structure of compounds 17-19 was established by spectroscopic analysis, and then chemically confirmed. Although compound 14 decomposed during the substitution reaction, the 4-p-nitrophenylsulfonyl derivative 15 gave a 2:1 mixture of the 4-thiocyano derivatives with inversion [methyl 4,6-dideoxy-4-thiocyano-α-d-talopyranoside (22)] and retention [methyl 4,6-dideoxy-4-thiocyano-α-d-mannopyranoside (23)] of the C-4 configuration. © 1991.

Registro:

Documento: Artículo
Título:Nucleophilic displacement-reactions of the 4-sulfonyloxy group in derivatives having the d-manno configuration
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
Palabras clave:carbohydrate derivative; sugar; article; chemical structure; nuclear magnetic resonance; synthesis
Año:1991
Volumen:211
Número:2
Página de inicio:295
Página de fin:308
DOI: http://dx.doi.org/10.1016/0008-6215(91)80099-9
Título revista:Carbohydrate Research
Título revista abreviado:Carbohydr. Res.
ISSN:00086215
CODEN:CRBRA
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00086215_v211_n2_p295_Cicero

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Citas:

---------- APA ----------
Cicero, D., Varela, O. & De Lederkremer, R.M. (1991) . Nucleophilic displacement-reactions of the 4-sulfonyloxy group in derivatives having the d-manno configuration. Carbohydrate Research, 211(2), 295-308.
http://dx.doi.org/10.1016/0008-6215(91)80099-9
---------- CHICAGO ----------
Cicero, D., Varela, O., De Lederkremer, R.M. "Nucleophilic displacement-reactions of the 4-sulfonyloxy group in derivatives having the d-manno configuration" . Carbohydrate Research 211, no. 2 (1991) : 295-308.
http://dx.doi.org/10.1016/0008-6215(91)80099-9
---------- MLA ----------
Cicero, D., Varela, O., De Lederkremer, R.M. "Nucleophilic displacement-reactions of the 4-sulfonyloxy group in derivatives having the d-manno configuration" . Carbohydrate Research, vol. 211, no. 2, 1991, pp. 295-308.
http://dx.doi.org/10.1016/0008-6215(91)80099-9
---------- VANCOUVER ----------
Cicero, D., Varela, O., De Lederkremer, R.M. Nucleophilic displacement-reactions of the 4-sulfonyloxy group in derivatives having the d-manno configuration. Carbohydr. Res. 1991;211(2):295-308.
http://dx.doi.org/10.1016/0008-6215(91)80099-9