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Abstract:

Two series of imidazo[2,1-b]thiazoles substituted on C-3 or C-5 with an unprotected carbohydrate moiety were synthesized. Different protective groups for position 3 of the carbohydrate moiety were tested (acetyl, tert-butyldimethylsilyl (TBDMS), and p-methoxybenzyl (PMB)) and the latter turn out to be the best strategy to obtain the desired products. Full deprotection of the carbohydrate was performed successfully in only one step. © 2012 Elsevier Ltd. All rights reserved.

Registro:

Documento: Artículo
Título:Synthesis of imidazo[2,1-b]thiazoles linked to an unprotected carbohydrate moiety
Autor:Barradas, J.S.; Errea, M.I.; D'Accorso, N.B.
Filiación:Departamento de Química Orgánica, Universidad de Buenos Aires, Ciudad Universitaria, 1428 Buenos Aires, Argentina
Departamento de Ingeniería Química, Instituto Tecnológico de Buenos Aires, Av. Eduardo Madero 399, 1106 Buenos Aires, Argentina
National Research Council of Argentina (CONICET), Argentina
Palabras clave:Carbohydrates; Heterocycles; Imidazo[2,1-b]thiazoles; Protective groups; Deprotection; Heterocycles; Imidazo[2,1-b]thiazoles; One step; P-methoxybenzyl; Protective group; Tert-butyldimethylsilyl; Organic compounds; Synthesis (chemical); Carbohydrates; acetic acid derivative; benzyl derivative; carbohydrate; heterocyclic compound; imidazo[2,1 b]thiazole derivative; silane derivative; article; carbohydrate synthesis; deprotection reaction; one pot synthesis; priority journal; quantum yield; reaction analysis; Carbohydrates; Imidazoles; Molecular Structure; Stereoisomerism; Thiazoles
Año:2012
Volumen:355
Página de inicio:79
Página de fin:86
DOI: http://dx.doi.org/10.1016/j.carres.2012.04.011
Título revista:Carbohydrate Research
Título revista abreviado:Carbohydr. Res.
ISSN:00086215
CODEN:CRBRA
CAS:Carbohydrates; Imidazoles; Thiazoles
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00086215_v355_n_p79_Barradas

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Citas:

---------- APA ----------
Barradas, J.S., Errea, M.I. & D'Accorso, N.B. (2012) . Synthesis of imidazo[2,1-b]thiazoles linked to an unprotected carbohydrate moiety. Carbohydrate Research, 355, 79-86.
http://dx.doi.org/10.1016/j.carres.2012.04.011
---------- CHICAGO ----------
Barradas, J.S., Errea, M.I., D'Accorso, N.B. "Synthesis of imidazo[2,1-b]thiazoles linked to an unprotected carbohydrate moiety" . Carbohydrate Research 355 (2012) : 79-86.
http://dx.doi.org/10.1016/j.carres.2012.04.011
---------- MLA ----------
Barradas, J.S., Errea, M.I., D'Accorso, N.B. "Synthesis of imidazo[2,1-b]thiazoles linked to an unprotected carbohydrate moiety" . Carbohydrate Research, vol. 355, 2012, pp. 79-86.
http://dx.doi.org/10.1016/j.carres.2012.04.011
---------- VANCOUVER ----------
Barradas, J.S., Errea, M.I., D'Accorso, N.B. Synthesis of imidazo[2,1-b]thiazoles linked to an unprotected carbohydrate moiety. Carbohydr. Res. 2012;355:79-86.
http://dx.doi.org/10.1016/j.carres.2012.04.011