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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1997
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| Acceso en línea: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_09574166_v8_n9_p1383_Orgueira http://hdl.handle.net/20.500.12110/paper_09574166_v8_n9_p1383_Orgueira |
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paper:paper_09574166_v8_n9_p1383_Orgueira2023-06-08T15:56:31Z Stereocontrolled synthesis of stereoregular, chiral analogs of nylon 5,5 and nylon 5,6 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. 1997 https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_09574166_v8_n9_p1383_Orgueira 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 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. |
| 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 |
| publishDate |
1997 |
| url |
https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_09574166_v8_n9_p1383_Orgueira http://hdl.handle.net/20.500.12110/paper_09574166_v8_n9_p1383_Orgueira |
| _version_ |
1768543238648496128 |