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Abstract:

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.

Registro:

Documento: Artículo
Título:Synthesis and characterization of poly-O-methyl-[n]-polyurethane from a d-glucamine-based monomer
Autor:Kolender, A.A.; Arce, S.M.; Varela, O.
Filiación:CIHIDECAR-CONICET, Departamento de Química Orgánica, Universidad de Buenos Aires, Pabellón 2, 1428 Buenos Aires, Argentina
Palabras clave: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
Año:2011
Volumen:346
Número:12
Página de inicio:1398
Página de fin:1405
DOI: http://dx.doi.org/10.1016/j.carres.2011.02.022
Título revista:Carbohydrate Research
Título revista abreviado:Carbohydr. Res.
ISSN:00086215
CODEN:CRBRA
CAS:polyurethan, 61789-63-7; Amines; Carbonates; Isocyanates; Polyurethanes; Sugar Alcohols
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00086215_v346_n12_p1398_Kolender

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Citas:

---------- APA ----------
Kolender, A.A., Arce, S.M. & Varela, O. (2011) . Synthesis and characterization of poly-O-methyl-[n]-polyurethane from a d-glucamine-based monomer. Carbohydrate Research, 346(12), 1398-1405.
http://dx.doi.org/10.1016/j.carres.2011.02.022
---------- CHICAGO ----------
Kolender, A.A., Arce, S.M., Varela, O. "Synthesis and characterization of poly-O-methyl-[n]-polyurethane from a d-glucamine-based monomer" . Carbohydrate Research 346, no. 12 (2011) : 1398-1405.
http://dx.doi.org/10.1016/j.carres.2011.02.022
---------- MLA ----------
Kolender, A.A., Arce, S.M., Varela, O. "Synthesis and characterization of poly-O-methyl-[n]-polyurethane from a d-glucamine-based monomer" . Carbohydrate Research, vol. 346, no. 12, 2011, pp. 1398-1405.
http://dx.doi.org/10.1016/j.carres.2011.02.022
---------- VANCOUVER ----------
Kolender, A.A., Arce, S.M., Varela, O. Synthesis and characterization of poly-O-methyl-[n]-polyurethane from a d-glucamine-based monomer. Carbohydr. Res. 2011;346(12):1398-1405.
http://dx.doi.org/10.1016/j.carres.2011.02.022