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Abstract:

An expeditious synthesis of cis-4-hydroxypipecolic acid (1) is described. The key step was diastereoselective hydrogenation of 2-acetamido-6-O-acetyl-2,3,5-trideoxy-hex-2-enono-1,4-lactone (3), obtained in three high yielding steps from D-glucosamine. The formation of the piperidine ring from 2-amino-2,3,5-trideoxy-threo-hexono-1,4-lactone derivative (10) was achieved by intramolecular nucleophilic displacement of the C-6 sulfonate by the C-2 amino group. © 1993.

Registro:

Documento: Artículo
Título:Diastereoselective synthesis of cis-4-hydroxypipecolic acid from D-glucosamine.
Autor:Nin, A.P.; Varela, O.; de Lederkremer, R.M.
Filiación:Departamento de Química Orgánica. Facultad de Ciencias Exactas, Naturales. Universidad de Buenos Aires. Ciudad Universitaria. Pabellón II, 1428 Buenos Aires, Argentina
Palabras clave:4 hydroxypipecolic acid; piperidine derivative; unclassified drug; article; drug structure; drug synthesis; nuclear magnetic resonance; reaction analysis; stereochemistry
Año:1993
Volumen:49
Número:42
Página de inicio:9459
Página de fin:9464
DOI: http://dx.doi.org/10.1016/S0040-4020(01)80215-5
Título revista:Tetrahedron
Título revista abreviado:Tetrahedron
ISSN:00404020
CODEN:TETRA
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00404020_v49_n42_p9459_Nin

Referencias:

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Citas:

---------- APA ----------
Nin, A.P., Varela, O. & de Lederkremer, R.M. (1993) . Diastereoselective synthesis of cis-4-hydroxypipecolic acid from D-glucosamine. Tetrahedron, 49(42), 9459-9464.
http://dx.doi.org/10.1016/S0040-4020(01)80215-5
---------- CHICAGO ----------
Nin, A.P., Varela, O., de Lederkremer, R.M. "Diastereoselective synthesis of cis-4-hydroxypipecolic acid from D-glucosamine." Tetrahedron 49, no. 42 (1993) : 9459-9464.
http://dx.doi.org/10.1016/S0040-4020(01)80215-5
---------- MLA ----------
Nin, A.P., Varela, O., de Lederkremer, R.M. "Diastereoselective synthesis of cis-4-hydroxypipecolic acid from D-glucosamine." Tetrahedron, vol. 49, no. 42, 1993, pp. 9459-9464.
http://dx.doi.org/10.1016/S0040-4020(01)80215-5
---------- VANCOUVER ----------
Nin, A.P., Varela, O., de Lederkremer, R.M. Diastereoselective synthesis of cis-4-hydroxypipecolic acid from D-glucosamine. Tetrahedron. 1993;49(42):9459-9464.
http://dx.doi.org/10.1016/S0040-4020(01)80215-5