Synthesis and polymerization of conveniently substituted 6-amino-6-deoxy-D-galactonic acid derivatives

Methyl 6-azido-6-deoxy-2,3:4,5-di-O-isopropylidene-D-galactonate (1), prepared in two steps from D-galactono-1,4-lactone, was hydrolyzed to the corresponding acid 2, which was esterified with phenol (PhOH) in the presence of dicyclohexylcarbodiimide (DCC) to give the phenyl ester 3. Hydrogenolysis o...

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Detalles Bibliográficos
Publicado: 2005
Materias:
Acetal
D-galactonic acid
Polyamide
Polymerization
Sugar amino acids
Acceso en línea:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_14246376_v2005_n12_p76_RomeroZaliz
http://hdl.handle.net/20.500.12110/paper_14246376_v2005_n12_p76_RomeroZaliz
Aporte de:
Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) de Universidad de Buenos Aires
id paper:paper_14246376_v2005_n12_p76_RomeroZaliz
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spelling paper:paper_14246376_v2005_n12_p76_RomeroZaliz2023-06-08T16:13:58Z Synthesis and polymerization of conveniently substituted 6-amino-6-deoxy-D-galactonic acid derivatives Acetal D-galactonic acid Polyamide Polymerization Sugar amino acids Methyl 6-azido-6-deoxy-2,3:4,5-di-O-isopropylidene-D-galactonate (1), prepared in two steps from D-galactono-1,4-lactone, was hydrolyzed to the corresponding acid 2, which was esterified with phenol (PhOH) in the presence of dicyclohexylcarbodiimide (DCC) to give the phenyl ester 3. Hydrogenolysis of the azide function of 3 yielded the hydrochloride derivative of the amino acid 4. Compound 4 is conveniently substituted for the polycondensation; therefore, this reaction was conducted using DMF as solvent and N,N-diisopropylethylamine as a basic catalyst. The MALDI-TOF mass spectrum of the isolated product (5) indicated that this was a mixture of the cyclic trimer (M + Na+, 793.7) and linear oligomers (from the tetramer to the tetradecamer). To favor the linear polymerization the dimeric amino acid 10 was prepared starting from 2. Thus, hydrogenation of 2 gave the amino acid 6, and treatment of 2 with pentachlorophenol-DCC gave the pentachlorophenyl ester 7. Coupling of 6 with 7 in the presence of DCC gave the dimer 8, which was converted (PhOH, DCC) into 9. Hydrogenolysis of 9 afforded the dimeric amino acid 10, which was polymerized under the conditions employed for 4. The resulting polyamide 11 was highly soluble in common organic solvents, and its molecular weight was established by MALDI-TOF MS and size exclusion chromatography (Mw = 2700). ©ARKAT. 2005 https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_14246376_v2005_n12_p76_RomeroZaliz http://hdl.handle.net/20.500.12110/paper_14246376_v2005_n12_p76_RomeroZaliz
institution Universidad de Buenos Aires
institution_str I-28
repository_str R-134
collection Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA)
topic Acetal
D-galactonic acid
Polyamide
Polymerization
Sugar amino acids
spellingShingle Acetal
D-galactonic acid
Polyamide
Polymerization
Sugar amino acids
Synthesis and polymerization of conveniently substituted 6-amino-6-deoxy-D-galactonic acid derivatives
topic_facet Acetal
D-galactonic acid
Polyamide
Polymerization
Sugar amino acids
description Methyl 6-azido-6-deoxy-2,3:4,5-di-O-isopropylidene-D-galactonate (1), prepared in two steps from D-galactono-1,4-lactone, was hydrolyzed to the corresponding acid 2, which was esterified with phenol (PhOH) in the presence of dicyclohexylcarbodiimide (DCC) to give the phenyl ester 3. Hydrogenolysis of the azide function of 3 yielded the hydrochloride derivative of the amino acid 4. Compound 4 is conveniently substituted for the polycondensation; therefore, this reaction was conducted using DMF as solvent and N,N-diisopropylethylamine as a basic catalyst. The MALDI-TOF mass spectrum of the isolated product (5) indicated that this was a mixture of the cyclic trimer (M + Na+, 793.7) and linear oligomers (from the tetramer to the tetradecamer). To favor the linear polymerization the dimeric amino acid 10 was prepared starting from 2. Thus, hydrogenation of 2 gave the amino acid 6, and treatment of 2 with pentachlorophenol-DCC gave the pentachlorophenyl ester 7. Coupling of 6 with 7 in the presence of DCC gave the dimer 8, which was converted (PhOH, DCC) into 9. Hydrogenolysis of 9 afforded the dimeric amino acid 10, which was polymerized under the conditions employed for 4. The resulting polyamide 11 was highly soluble in common organic solvents, and its molecular weight was established by MALDI-TOF MS and size exclusion chromatography (Mw = 2700). ©ARKAT.
title Synthesis and polymerization of conveniently substituted 6-amino-6-deoxy-D-galactonic acid derivatives
title_short Synthesis and polymerization of conveniently substituted 6-amino-6-deoxy-D-galactonic acid derivatives
title_full Synthesis and polymerization of conveniently substituted 6-amino-6-deoxy-D-galactonic acid derivatives
title_fullStr Synthesis and polymerization of conveniently substituted 6-amino-6-deoxy-D-galactonic acid derivatives
title_full_unstemmed Synthesis and polymerization of conveniently substituted 6-amino-6-deoxy-D-galactonic acid derivatives
title_sort synthesis and polymerization of conveniently substituted 6-amino-6-deoxy-d-galactonic acid derivatives
publishDate 2005
url https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_14246376_v2005_n12_p76_RomeroZaliz
http://hdl.handle.net/20.500.12110/paper_14246376_v2005_n12_p76_RomeroZaliz
_version_ 1768546601609986048

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