Stereocontrolled synthesis of stereoregular, chiral analogs of nylon 5,5 and nylon 5,6

L-glutamic acid (1) was employed as a chiral template in the preparation of the pentachlorophenyl ester of (4S)-carboxy-1,4-butirolactone (3), a key precursor of chiral analogs of nylon 5,5 and nylon 5,6. Stereocontrol in the synthesis of these polymers was achieved by chemoselective condensation of...

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Autores principales: Orgueira, H.A., Varela, O.
Formato: JOUR
Materias:
nylon
polymer
article
chirality
drug synthesis
in vitro study
nuclear magnetic resonance spectroscopy
priority journal
reaction analysis
stereochemistry
Acceso en línea:http://hdl.handle.net/20.500.12110/paper_09574166_v8_n9_p1383_Orgueira
Aporte de:
Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) de Universidad de Buenos Aires
id todo:paper_09574166_v8_n9_p1383_Orgueira
record_format dspace
spelling todo:paper_09574166_v8_n9_p1383_Orgueira2023-10-03T15:52:27Z Stereocontrolled synthesis of stereoregular, chiral analogs of nylon 5,5 and nylon 5,6 Orgueira, H.A. Varela, O. nylon polymer article chirality drug synthesis in vitro study nuclear magnetic resonance spectroscopy priority journal reaction analysis stereochemistry L-glutamic acid (1) was employed as a chiral template in the preparation of the pentachlorophenyl ester of (4S)-carboxy-1,4-butirolactone (3), a key precursor of chiral analogs of nylon 5,5 and nylon 5,6. Stereocontrol in the synthesis of these polymers was achieved by chemoselective condensation of the ester group of 3 with aminoalcohols. The alcohol function of the resulting N-(hydroxyalkyl)amides (4 and 9) was converted into amine by tosylation, azide substitution and hydrogenolysis. The amino lactones 7 and 12 thus obtained were conveniently functionalized for the polycondensation, which led to the stereoregular, crystalline polyamides 8 and 13. JOUR info:eu-repo/semantics/openAccess http://creativecommons.org/licenses/by/2.5/ar http://hdl.handle.net/20.500.12110/paper_09574166_v8_n9_p1383_Orgueira
institution Universidad de Buenos Aires
institution_str I-28
repository_str R-134
collection Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA)
topic nylon
polymer
article
chirality
drug synthesis
in vitro study
nuclear magnetic resonance spectroscopy
priority journal
reaction analysis
stereochemistry
spellingShingle nylon
polymer
article
chirality
drug synthesis
in vitro study
nuclear magnetic resonance spectroscopy
priority journal
reaction analysis
stereochemistry
Orgueira, H.A.
Varela, O.
Stereocontrolled synthesis of stereoregular, chiral analogs of nylon 5,5 and nylon 5,6
topic_facet nylon
polymer
article
chirality
drug synthesis
in vitro study
nuclear magnetic resonance spectroscopy
priority journal
reaction analysis
stereochemistry
description L-glutamic acid (1) was employed as a chiral template in the preparation of the pentachlorophenyl ester of (4S)-carboxy-1,4-butirolactone (3), a key precursor of chiral analogs of nylon 5,5 and nylon 5,6. Stereocontrol in the synthesis of these polymers was achieved by chemoselective condensation of the ester group of 3 with aminoalcohols. The alcohol function of the resulting N-(hydroxyalkyl)amides (4 and 9) was converted into amine by tosylation, azide substitution and hydrogenolysis. The amino lactones 7 and 12 thus obtained were conveniently functionalized for the polycondensation, which led to the stereoregular, crystalline polyamides 8 and 13.
format JOUR
author Orgueira, H.A.
Varela, O.
author_facet Orgueira, H.A.
Varela, O.
author_sort Orgueira, H.A.
title Stereocontrolled synthesis of stereoregular, chiral analogs of nylon 5,5 and nylon 5,6
title_short Stereocontrolled synthesis of stereoregular, chiral analogs of nylon 5,5 and nylon 5,6
title_full Stereocontrolled synthesis of stereoregular, chiral analogs of nylon 5,5 and nylon 5,6
title_fullStr Stereocontrolled synthesis of stereoregular, chiral analogs of nylon 5,5 and nylon 5,6
title_full_unstemmed Stereocontrolled synthesis of stereoregular, chiral analogs of nylon 5,5 and nylon 5,6
title_sort stereocontrolled synthesis of stereoregular, chiral analogs of nylon 5,5 and nylon 5,6
url http://hdl.handle.net/20.500.12110/paper_09574166_v8_n9_p1383_Orgueira
work_keys_str_mv AT orgueiraha stereocontrolledsynthesisofstereoregularchiralanalogsofnylon55andnylon56
AT varelao stereocontrolledsynthesisofstereoregularchiralanalogsofnylon55andnylon56
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