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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Autores principales:	Nin, A.P., Varela, O., de Lederkremer, R.M.
Formato:	JOUR
Materias:	4 hydroxypipecolic acid piperidine derivative unclassified drug article drug structure drug synthesis nuclear magnetic resonance reaction analysis stereochemistry
Acceso en línea:	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	todo:paper_00404020_v49_n42_p9459_Nin
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spelling	todo:paper_00404020_v49_n42_p9459_Nin2023-10-03T14:50:36Z Diastereoselective synthesis of cis-4-hydroxypipecolic acid from D-glucosamine. Nin, A.P. Varela, O. de Lederkremer, R.M. 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. JOUR info:eu-repo/semantics/openAccess http://creativecommons.org/licenses/by/2.5/ar 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, A.P. Varela, O. de Lederkremer, R.M. 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.
format	JOUR
author	Nin, A.P. Varela, O. de Lederkremer, R.M.
author_facet	Nin, A.P. Varela, O. de Lederkremer, R.M.
author_sort	Nin, A.P.
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.
url	http://hdl.handle.net/20.500.12110/paper_00404020_v49_n42_p9459_Nin
work_keys_str_mv	AT ninap diastereoselectivesynthesisofcis4hydroxypipecolicacidfromdglucosamine AT varelao diastereoselectivesynthesisofcis4hydroxypipecolicacidfromdglucosamine AT delederkremerrm diastereoselectivesynthesisofcis4hydroxypipecolicacidfromdglucosamine
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Diastereoselective synthesis of cis-4-hydroxypipecolic acid from D-glucosamine.

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