Diastereoselective synthesis of cis-4-hydroxypipecolic acid from D-glucosamine.

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-amin...

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Detalles Bibliográficos
Autores principales:	Nin, Alejandro Pablo, Varela, Oscar José, Muchnik de Lederkremer, Rosa María
Publicado:	1993
Materias:	4 hydroxypipecolic acid piperidine derivative unclassified drug article drug structure drug synthesis nuclear magnetic resonance reaction analysis stereochemistry
Acceso en línea:	https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00404020_v49_n42_p9459_Nin http://hdl.handle.net/20.500.12110/paper_00404020_v49_n42_p9459_Nin
Aporte de:	Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) de Universidad de Buenos Aires

id	paper:paper_00404020_v49_n42_p9459_Nin
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spelling	paper:paper_00404020_v49_n42_p9459_Nin2023-06-08T15:04:11Z Diastereoselective synthesis of cis-4-hydroxypipecolic acid from D-glucosamine. Nin, Alejandro Pablo Varela, Oscar José Muchnik de Lederkremer, Rosa María 4 hydroxypipecolic acid piperidine derivative unclassified drug article drug structure drug synthesis nuclear magnetic resonance reaction analysis stereochemistry 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. Fil:Nin, A.P. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Varela, O. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:de Lederkremer, R.M. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. 1993 https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00404020_v49_n42_p9459_Nin http://hdl.handle.net/20.500.12110/paper_00404020_v49_n42_p9459_Nin
institution	Universidad de Buenos Aires
institution_str	I-28
repository_str	R-134
collection	Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA)
topic	4 hydroxypipecolic acid piperidine derivative unclassified drug article drug structure drug synthesis nuclear magnetic resonance reaction analysis stereochemistry
spellingShingle	4 hydroxypipecolic acid piperidine derivative unclassified drug article drug structure drug synthesis nuclear magnetic resonance reaction analysis stereochemistry Nin, Alejandro Pablo Varela, Oscar José Muchnik de Lederkremer, Rosa María Diastereoselective synthesis of cis-4-hydroxypipecolic acid from D-glucosamine.
topic_facet	4 hydroxypipecolic acid piperidine derivative unclassified drug article drug structure drug synthesis nuclear magnetic resonance reaction analysis stereochemistry
description	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.
author	Nin, Alejandro Pablo Varela, Oscar José Muchnik de Lederkremer, Rosa María
author_facet	Nin, Alejandro Pablo Varela, Oscar José Muchnik de Lederkremer, Rosa María
author_sort	Nin, Alejandro Pablo
title	Diastereoselective synthesis of cis-4-hydroxypipecolic acid from D-glucosamine.
title_short	Diastereoselective synthesis of cis-4-hydroxypipecolic acid from D-glucosamine.
title_full	Diastereoselective synthesis of cis-4-hydroxypipecolic acid from D-glucosamine.
title_fullStr	Diastereoselective synthesis of cis-4-hydroxypipecolic acid from D-glucosamine.
title_full_unstemmed	Diastereoselective synthesis of cis-4-hydroxypipecolic acid from D-glucosamine.
title_sort	diastereoselective synthesis of cis-4-hydroxypipecolic acid from d-glucosamine.
publishDate	1993
url	https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00404020_v49_n42_p9459_Nin http://hdl.handle.net/20.500.12110/paper_00404020_v49_n42_p9459_Nin
work_keys_str_mv	AT ninalejandropablo diastereoselectivesynthesisofcis4hydroxypipecolicacidfromdglucosamine AT varelaoscarjose diastereoselectivesynthesisofcis4hydroxypipecolicacidfromdglucosamine AT muchnikdelederkremerrosamaria diastereoselectivesynthesisofcis4hydroxypipecolicacidfromdglucosamine
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Diastereoselective synthesis of cis-4-hydroxypipecolic acid from D-glucosamine.

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