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Abstract:

An enantiospecific synthesis of the tetrahydrofuran amino acid (2S,5S)-5-(aminomethyl)-tetrahydrofuran-2-carboxylic acid 1 is reported. The sugar enone 2-(S)-octyl 6-O-acetyl-3,4-dideoxy-α-d-glycero-hex-3- enopyranosid-2-ulose 2a, derived from galactose, was employed as a chiral precursor. The enone 2a was converted by chemical manipulation of the functional groups into the 6-azido-2-O-tosyl-3,4,6-trideoxy-d-erythro-hexono-1,5-lactone 9 as key intermediate. Methanolysis of 9 induced the opening of the lactone and the attack of the hydroxyl group at C-5 to C-2 with the displacement of the tosylate. This reaction led to the formation of the tetrahydrofuran ring of methyl (2S,5S)-5-(azidomethyl)-tetrahydrofuran-2-carboxylate 10, which was readily converted into 1. The overall yield of the sequence was 35%, and all the intermediates and the final product have been fully characterized. In addition, the preferential conformations in solution of lactone 9 and target molecule 1 have been established. © 2010 Elsevier Ltd. All rights reserved.

Registro:

Documento: Artículo
Título:Enantiospecific synthesis of the sugar amino acid (2S,5S)-5-(aminomethyl)- tetrahydrofuran-2-carboxylic acid
Autor:Uhrig, M.L.; Simirgiotis, M.J.; Varela, O.
Filiación:CIHIDECAR-CONICET, Departamento de Química Orgánica, Universidad de Buenos Aires, Argentina
Palabras clave:2 propyl 3,4 dideoxy alpha dextro erythro hexopyranoside; 5 (aminomethyl)tetrahydrofuran 2 carboxylic acid; 5 (azidomethyl) tetrahydrofuran 2 carboxylate; 5 (azidomethyl)tetrahydrofuran 2 carboxylic acid; 6 azido 2 o tosyl 3,4,6 trideoxy alpha beta dextro erythro hexopyranose; 6 azido 2 o tosyl 3,4,6 trideoxy dextro erythro hexono 1,5 lactone; aminosugar; galactose; lactone; octyl 2,6 di o tosyl 3,4 dideoxy alpha dextro erythro hexopyranoside; octyl 3,4 dideoxy alpha dextro erythro hexopyranoside; octyl 6 azido 2 o tosyl 3,4,6 trideoxy alpha dextro erythro hexopyranoside; octyl 6 o acetyl 3,4 dideoxy alpha dextro glycero hex 3 enopyranosid 2 ulose; octyl 6 o acetyl 3,4 dideoxy alpha dextro glycerohex 3 enopyranosid 2 ulose; unclassified drug; article; chemical reaction kinetics; diastereoisomer; drug structure; drug synthesis; hydrolysis; methanolysis; priority journal; proton nuclear magnetic resonance; stereochemistry
Año:2010
Volumen:21
Número:19
Página de inicio:2435
Página de fin:2440
DOI: http://dx.doi.org/10.1016/j.tetasy.2010.08.013
Título revista:Tetrahedron Asymmetry
Título revista abreviado:Tetrahedron Asymmetry
ISSN:09574166
CODEN:TASYE
CAS:galactose, 26566-61-0, 50855-33-9, 59-23-4; lactone, 1338-03-0
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_09574166_v21_n19_p2435_Uhrig

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Citas:

---------- APA ----------
Uhrig, M.L., Simirgiotis, M.J. & Varela, O. (2010) . Enantiospecific synthesis of the sugar amino acid (2S,5S)-5-(aminomethyl)- tetrahydrofuran-2-carboxylic acid. Tetrahedron Asymmetry, 21(19), 2435-2440.
http://dx.doi.org/10.1016/j.tetasy.2010.08.013
---------- CHICAGO ----------
Uhrig, M.L., Simirgiotis, M.J., Varela, O. "Enantiospecific synthesis of the sugar amino acid (2S,5S)-5-(aminomethyl)- tetrahydrofuran-2-carboxylic acid" . Tetrahedron Asymmetry 21, no. 19 (2010) : 2435-2440.
http://dx.doi.org/10.1016/j.tetasy.2010.08.013
---------- MLA ----------
Uhrig, M.L., Simirgiotis, M.J., Varela, O. "Enantiospecific synthesis of the sugar amino acid (2S,5S)-5-(aminomethyl)- tetrahydrofuran-2-carboxylic acid" . Tetrahedron Asymmetry, vol. 21, no. 19, 2010, pp. 2435-2440.
http://dx.doi.org/10.1016/j.tetasy.2010.08.013
---------- VANCOUVER ----------
Uhrig, M.L., Simirgiotis, M.J., Varela, O. Enantiospecific synthesis of the sugar amino acid (2S,5S)-5-(aminomethyl)- tetrahydrofuran-2-carboxylic acid. Tetrahedron Asymmetry. 2010;21(19):2435-2440.
http://dx.doi.org/10.1016/j.tetasy.2010.08.013