Synthesis and characterization of poly-O-methyl-[n]-polyurethane from a d-glucamine-based monomer
Aminoalditol 1-amino-1-deoxy-d-sorbitol (1) was readily converted into 2,3,4,5-tetra-O-methyl derivative 5, a key precursor of a sugar-based [n]-polyurethane. For the polymerization, the free amino or primary hydroxyl groups of 5 were selectively activated and employed as starting monomers in two al...
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2011
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| Acceso en línea: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00086215_v346_n12_p1398_Kolender http://hdl.handle.net/20.500.12110/paper_00086215_v346_n12_p1398_Kolender |
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paper:paper_00086215_v346_n12_p1398_Kolender2023-06-08T14:32:58Z Synthesis and characterization of poly-O-methyl-[n]-polyurethane from a d-glucamine-based monomer α-Amino-ω-phenylcarbonate [n]-Polyurethane Alditol isocyanate Biomaterial Chiral d-Glucamine [n]-Polyurethane Acetylacetonates Alditol isocyanate Alternative procedures Alternative synthesis Chiral d-Glucamine Ethyl acetates Free hydroxyl groups Hydroxyl groups In-situ Metal catalyst Resulting materials Acetone Alcohols Amorphous materials Biological materials Catalysts Molecular weight Monomers Organic solvents Polymerization Polymers Urea Zirconium Amino sugars 1 (n tert butoxycarbonylamino) 1 deoxy 2,3,4,5 tetra o 6 o phenyloxycarbonyl dextro sorbitol 1 (n tert butoxycarbonylamino) 1 deoxy 2,3,4,5 tetra o methyl dextro sorbitol 1 amino 1 deoxy 2,3,4,5 tetra o methyl 6 o phenyloxycarbonyl dextro sorbitol hydrochloride 1 amino 1 deoxy 2,3,4,5 tetra o methyl dextro sorbitol 1 deoxy 1 (n methyl, n tritylamino) 2,3,4,5 tetra o methyl 6 o trityl dextro sorbitol 1 deoxy 2,3,4,5 tetra o methyl 6 o trityl 1 n tritylamino dextro sorbitol 1 deoxy 6 o trityl 1 n tritylamino dextro sorbitol dextro glucamine monomer poly o methyl [n] polyurethane polyurethan unclassified drug article carbohydrate analysis carbohydrate synthesis gel permeation chromatography mass spectrometry priority journal proton nuclear magnetic resonance Amines Biodegradation, Environmental Carbonates Chemistry, Organic Chromatography, Gel Isocyanates Polymerization Polyurethanes Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization Stereoisomerism Sugar Alcohols Thermogravimetry Tetra Aminoalditol 1-amino-1-deoxy-d-sorbitol (1) was readily converted into 2,3,4,5-tetra-O-methyl derivative 5, a key precursor of a sugar-based [n]-polyurethane. For the polymerization, the free amino or primary hydroxyl groups of 5 were selectively activated and employed as starting monomers in two alternative procedures. Thus, the amino function of 5 was converted into the isocyanate derivative by treatment with di-tert-butyltricarbonate, and polymerized in situ in the presence of Zr(IV) acetylacetonate. The resulting poly(1-amino-1-deoxy-2,3,4,5-tetra-O-methyl-d-sorbitol)urethane (8) had a moderate molecular weight and showed the presence of urea units. The alternative synthesis of 8 involved the activation of the free hydroxyl group of 5 as the corresponding phenylcarbonate. The polymerization of this α-amino-ω- phenylcarbonate alditol monomer does not require a metal catalyst. The resulting material exhibited an improved molecular weight and higher purity than that obtained via the isocyanate. [n]-polyurethane 8 was highly soluble in water as well as in common organic solvents (chloroform, acetone, ethyl acetate, etc) and was obtained as an amorphous material which was characterized thermally and spectroscopically. © 2011 Elsevier Ltd. All rights reserved. 2011 https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00086215_v346_n12_p1398_Kolender http://hdl.handle.net/20.500.12110/paper_00086215_v346_n12_p1398_Kolender |
| institution |
Universidad de Buenos Aires |
| institution_str |
I-28 |
| repository_str |
R-134 |
| collection |
Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) |
| topic |
α-Amino-ω-phenylcarbonate [n]-Polyurethane Alditol isocyanate Biomaterial Chiral d-Glucamine [n]-Polyurethane Acetylacetonates Alditol isocyanate Alternative procedures Alternative synthesis Chiral d-Glucamine Ethyl acetates Free hydroxyl groups Hydroxyl groups In-situ Metal catalyst Resulting materials Acetone Alcohols Amorphous materials Biological materials Catalysts Molecular weight Monomers Organic solvents Polymerization Polymers Urea Zirconium Amino sugars 1 (n tert butoxycarbonylamino) 1 deoxy 2,3,4,5 tetra o 6 o phenyloxycarbonyl dextro sorbitol 1 (n tert butoxycarbonylamino) 1 deoxy 2,3,4,5 tetra o methyl dextro sorbitol 1 amino 1 deoxy 2,3,4,5 tetra o methyl 6 o phenyloxycarbonyl dextro sorbitol hydrochloride 1 amino 1 deoxy 2,3,4,5 tetra o methyl dextro sorbitol 1 deoxy 1 (n methyl, n tritylamino) 2,3,4,5 tetra o methyl 6 o trityl dextro sorbitol 1 deoxy 2,3,4,5 tetra o methyl 6 o trityl 1 n tritylamino dextro sorbitol 1 deoxy 6 o trityl 1 n tritylamino dextro sorbitol dextro glucamine monomer poly o methyl [n] polyurethane polyurethan unclassified drug article carbohydrate analysis carbohydrate synthesis gel permeation chromatography mass spectrometry priority journal proton nuclear magnetic resonance Amines Biodegradation, Environmental Carbonates Chemistry, Organic Chromatography, Gel Isocyanates Polymerization Polyurethanes Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization Stereoisomerism Sugar Alcohols Thermogravimetry Tetra |
| spellingShingle |
α-Amino-ω-phenylcarbonate [n]-Polyurethane Alditol isocyanate Biomaterial Chiral d-Glucamine [n]-Polyurethane Acetylacetonates Alditol isocyanate Alternative procedures Alternative synthesis Chiral d-Glucamine Ethyl acetates Free hydroxyl groups Hydroxyl groups In-situ Metal catalyst Resulting materials Acetone Alcohols Amorphous materials Biological materials Catalysts Molecular weight Monomers Organic solvents Polymerization Polymers Urea Zirconium Amino sugars 1 (n tert butoxycarbonylamino) 1 deoxy 2,3,4,5 tetra o 6 o phenyloxycarbonyl dextro sorbitol 1 (n tert butoxycarbonylamino) 1 deoxy 2,3,4,5 tetra o methyl dextro sorbitol 1 amino 1 deoxy 2,3,4,5 tetra o methyl 6 o phenyloxycarbonyl dextro sorbitol hydrochloride 1 amino 1 deoxy 2,3,4,5 tetra o methyl dextro sorbitol 1 deoxy 1 (n methyl, n tritylamino) 2,3,4,5 tetra o methyl 6 o trityl dextro sorbitol 1 deoxy 2,3,4,5 tetra o methyl 6 o trityl 1 n tritylamino dextro sorbitol 1 deoxy 6 o trityl 1 n tritylamino dextro sorbitol dextro glucamine monomer poly o methyl [n] polyurethane polyurethan unclassified drug article carbohydrate analysis carbohydrate synthesis gel permeation chromatography mass spectrometry priority journal proton nuclear magnetic resonance Amines Biodegradation, Environmental Carbonates Chemistry, Organic Chromatography, Gel Isocyanates Polymerization Polyurethanes Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization Stereoisomerism Sugar Alcohols Thermogravimetry Tetra Synthesis and characterization of poly-O-methyl-[n]-polyurethane from a d-glucamine-based monomer |
| topic_facet |
α-Amino-ω-phenylcarbonate [n]-Polyurethane Alditol isocyanate Biomaterial Chiral d-Glucamine [n]-Polyurethane Acetylacetonates Alditol isocyanate Alternative procedures Alternative synthesis Chiral d-Glucamine Ethyl acetates Free hydroxyl groups Hydroxyl groups In-situ Metal catalyst Resulting materials Acetone Alcohols Amorphous materials Biological materials Catalysts Molecular weight Monomers Organic solvents Polymerization Polymers Urea Zirconium Amino sugars 1 (n tert butoxycarbonylamino) 1 deoxy 2,3,4,5 tetra o 6 o phenyloxycarbonyl dextro sorbitol 1 (n tert butoxycarbonylamino) 1 deoxy 2,3,4,5 tetra o methyl dextro sorbitol 1 amino 1 deoxy 2,3,4,5 tetra o methyl 6 o phenyloxycarbonyl dextro sorbitol hydrochloride 1 amino 1 deoxy 2,3,4,5 tetra o methyl dextro sorbitol 1 deoxy 1 (n methyl, n tritylamino) 2,3,4,5 tetra o methyl 6 o trityl dextro sorbitol 1 deoxy 2,3,4,5 tetra o methyl 6 o trityl 1 n tritylamino dextro sorbitol 1 deoxy 6 o trityl 1 n tritylamino dextro sorbitol dextro glucamine monomer poly o methyl [n] polyurethane polyurethan unclassified drug article carbohydrate analysis carbohydrate synthesis gel permeation chromatography mass spectrometry priority journal proton nuclear magnetic resonance Amines Biodegradation, Environmental Carbonates Chemistry, Organic Chromatography, Gel Isocyanates Polymerization Polyurethanes Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization Stereoisomerism Sugar Alcohols Thermogravimetry Tetra |
| description |
Aminoalditol 1-amino-1-deoxy-d-sorbitol (1) was readily converted into 2,3,4,5-tetra-O-methyl derivative 5, a key precursor of a sugar-based [n]-polyurethane. For the polymerization, the free amino or primary hydroxyl groups of 5 were selectively activated and employed as starting monomers in two alternative procedures. Thus, the amino function of 5 was converted into the isocyanate derivative by treatment with di-tert-butyltricarbonate, and polymerized in situ in the presence of Zr(IV) acetylacetonate. The resulting poly(1-amino-1-deoxy-2,3,4,5-tetra-O-methyl-d-sorbitol)urethane (8) had a moderate molecular weight and showed the presence of urea units. The alternative synthesis of 8 involved the activation of the free hydroxyl group of 5 as the corresponding phenylcarbonate. The polymerization of this α-amino-ω- phenylcarbonate alditol monomer does not require a metal catalyst. The resulting material exhibited an improved molecular weight and higher purity than that obtained via the isocyanate. [n]-polyurethane 8 was highly soluble in water as well as in common organic solvents (chloroform, acetone, ethyl acetate, etc) and was obtained as an amorphous material which was characterized thermally and spectroscopically. © 2011 Elsevier Ltd. All rights reserved. |
| title |
Synthesis and characterization of poly-O-methyl-[n]-polyurethane from a d-glucamine-based monomer |
| title_short |
Synthesis and characterization of poly-O-methyl-[n]-polyurethane from a d-glucamine-based monomer |
| title_full |
Synthesis and characterization of poly-O-methyl-[n]-polyurethane from a d-glucamine-based monomer |
| title_fullStr |
Synthesis and characterization of poly-O-methyl-[n]-polyurethane from a d-glucamine-based monomer |
| title_full_unstemmed |
Synthesis and characterization of poly-O-methyl-[n]-polyurethane from a d-glucamine-based monomer |
| title_sort |
synthesis and characterization of poly-o-methyl-[n]-polyurethane from a d-glucamine-based monomer |
| publishDate |
2011 |
| url |
https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00086215_v346_n12_p1398_Kolender http://hdl.handle.net/20.500.12110/paper_00086215_v346_n12_p1398_Kolender |
| _version_ |
1768541684649426944 |