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Abstract:

Polyhydroxy [n]-polyurethanes with chains formed by sugar-derived units have been synthesized. The enantiomerically pure monomeric precursor 1-amino-1-deoxy-2,3:4,5-di-O-isopropylidene-Dgalactitol (4) was prepared from D-galactono-1,4-lactone (1) by a three-step route. Acetonation of 1 with 2,2-dimethoxypropane gave methyl 2,3:4,5-di-O-isopropyldene-D-galactonate (2). The ester group of 2 was converted into the amide and reduced with LiAlH 4 to afford 4. This amino alditol was treated with di-tertbutyltricarbonate to produce the intermediate isocyanate derivative as activated monomer for the polymerization. The reaction conditions were adjusted to prevent the formation of urea linkages during the polycondensation. Thus, polymerization of the isocyanate monomer in THF and in the presence of Zr(acac)4 as catalyst afforded the linear [n]-polyurethane 6, which upon purification was practically free of urea linkages. Removal of the acetal protecting groups of 6 with 10:1 TFA-water, under conditions that did not produce hydrolysis of the polymer chain, led to the polyhydroxy [n]-polyurethane 8, having all the hydroxyl groups free. Polyurethanes 6 and 8 are examples of polyhydroxy [n]-polyurethanes entirely obtained from a sugar precursor. They were isolated as crystalline materials that exhibited high melting temperatures and thermal stability up to 230 °C. Accordingly, the SEM analysis of 6 and 8 revealed surfaces with morphologies characteristic of crystalline polymers. © 2009 American Chemical Society.

Registro:

Documento: Artículo
Título:Synthesis of polyhydroxy [n]-polyurethanes derived from a carbohydrate precursor
Autor:Gómez, R.V.; Varela, O.
Filiación:Cihidecar-conicet, Departamento de Química Orgánica, Ciudad Universitaria, Pabellón 2, 1428 Buenos Aires, Argentina
Palabras clave:Activated monomers; Crystalline polymers; Ester groups; High melting; Hydroxyl groups; Isocyanate monomers; Isopropylidene; Monomeric precursors; Polymer chains; Protecting group; Reaction conditions; SEM analysis; Thermal stability; Amides; Amination; Amines; Chains; Crystalline materials; Esters; Melting point; Metabolism; Monomers; Polycondensation; Polymer melts; Polymers; Polyurethanes; Sugar (sucrose); Sugars; Synthesis (chemical); Urea; Zirconium; Biological membranes
Año:2009
Volumen:42
Número:21
Página de inicio:8112
Página de fin:8117
DOI: http://dx.doi.org/10.1021/ma9014643
Título revista:Macromolecules
Título revista abreviado:Macromolecules
ISSN:00249297
CODEN:MAMOB
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00249297_v42_n21_p8112_Gomez

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Citas:

---------- APA ----------
Gómez, R.V. & Varela, O. (2009) . Synthesis of polyhydroxy [n]-polyurethanes derived from a carbohydrate precursor. Macromolecules, 42(21), 8112-8117.
http://dx.doi.org/10.1021/ma9014643
---------- CHICAGO ----------
Gómez, R.V., Varela, O. "Synthesis of polyhydroxy [n]-polyurethanes derived from a carbohydrate precursor" . Macromolecules 42, no. 21 (2009) : 8112-8117.
http://dx.doi.org/10.1021/ma9014643
---------- MLA ----------
Gómez, R.V., Varela, O. "Synthesis of polyhydroxy [n]-polyurethanes derived from a carbohydrate precursor" . Macromolecules, vol. 42, no. 21, 2009, pp. 8112-8117.
http://dx.doi.org/10.1021/ma9014643
---------- VANCOUVER ----------
Gómez, R.V., Varela, O. Synthesis of polyhydroxy [n]-polyurethanes derived from a carbohydrate precursor. Macromolecules. 2009;42(21):8112-8117.
http://dx.doi.org/10.1021/ma9014643