Facile synthesis of a d-galactono-1,6-lactone derivative, a precursor of a copolyester

2,3,4,6-Tetra-O-methyl-d-galactonic acid (5) was readily prepared from d-galactono-1,4-lactone (1) in 47% yield. The sequence involves tritylation of HO-6 of 1, followed by O-permethylation and deprotection. Lactonization of 5 led to the per-O-methyl-d-galactono-1,6-lactone, which was copolymerized...

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Autor principal: Romero Zaliz, C.L
Otros Autores: Varela, O.
Formato: Capítulo de libro
Lenguaje:Inglés
Publicado: 2006
Acceso en línea:Registro en Scopus
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024 7 |2 scopus  |a 2-s2.0-33751270857 
024 7 |2 cas  |a trifluoromethanesulfonic acid, 1493-13-6; caprolactone, 502-44-3; galactonic acid, 13382-27-9; galactonolactone, 2426-46-2; Hexanoic Acids; Lactones; Polyesters; Sugar Acids 
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100 1 |a Romero Zaliz, C.L. 
245 1 0 |a Facile synthesis of a d-galactono-1,6-lactone derivative, a precursor of a copolyester 
260 |c 2006 
270 1 0 |m Varela, O.; CIHIDECAR, CONICET, Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Pabellón II, 1428-Buenos Aires, Argentina; email: varela@qo.fcen.uba.ar 
506 |2 openaire  |e Política editorial 
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504 |a Molina Pinilla, I., Bueno Martínez, M., Galbis, J.A., (2003) Carbohydr. Res., 338, pp. 549-555 
504 |a Romero Zaliz, C.L., Varela, O., (2003) Tetrahedron: Asymmetry, 14, pp. 2579-2586 
504 |a Romero Zaliz, C.L., Varela, O., (2005) Tetrahedron: Asymmetry, 16, pp. 97-103 
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520 3 |a 2,3,4,6-Tetra-O-methyl-d-galactonic acid (5) was readily prepared from d-galactono-1,4-lactone (1) in 47% yield. The sequence involves tritylation of HO-6 of 1, followed by O-permethylation and deprotection. Lactonization of 5 led to the per-O-methyl-d-galactono-1,6-lactone, which was copolymerized with ε-caprolactone by ring-opening polymerization catalyzed by scandium triflate. The incorporation of the sugar comonomer into the polyester chain was about 10%. © 2006 Elsevier Ltd. All rights reserved.  |l eng 
536 |a Detalles de la financiación: Universidad de Buenos Aires, X059 
536 |a Detalles de la financiación: National Science and Technology Development Agency 
536 |a Detalles de la financiación: National Council for Scientific Research 
536 |a Detalles de la financiación: Agencia Nacional de Promoción Científica y Tecnológica, 13922 
536 |a Detalles de la financiación: Consejo Nacional de Investigaciones Científicas y Técnicas, PIP 5011 
536 |a Detalles de la financiación: Support of our work by the University of Buenos Aires (project X059), the National Research Council of Argentina (CONICET, project PIP 5011) and the National Agency for Promotion of Science and Technology (ANPCyT, project 13922) is gratefully acknowledged. We thank Dr. Rosa Erra-Balsells and Dr. Hiroshi Nonami (Ehime University, Japan) for the MALDI-TOF mass spectra. O.V. is a Research Member of CONICET. 
593 |a CIHIDECAR, CONICET, Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Pabellón II, 1428-Buenos Aires, Argentina 
690 1 0 |a Ε-CAPROLACTONE 
690 1 0 |a ALDONO-1,6-LACTONE 
690 1 0 |a COPOLYESTER 
690 1 0 |a D-GALACTONO-1,4-LACTONE 
690 1 0 |a DERIVATIVES 
690 1 0 |a MONOMERS 
690 1 0 |a ORGANIC ACIDS 
690 1 0 |a POLYESTERS 
690 1 0 |a POLYMERIZATION 
690 1 0 |a SUGAR (SUCROSE) 
690 1 0 |a Ε-CAPROLACTONE 
690 1 0 |a ALDONO-1,6-LACTONE 
690 1 0 |a COPOLYESTERS 
690 1 0 |a D-GALACTONO-1,4-LACTONE 
690 1 0 |a KETONES 
690 1 0 |a 2,3,4,6 TETRA O METHYL DEXTRO GALACTONIC ACID 
690 1 0 |a DEXTRO GALACTONO 1,4 LACTONE 
690 1 0 |a EPSILON CAPROLACTONE 
690 1 0 |a LACTONE DERIVATIVE 
690 1 0 |a PER O METHYL DEXTRO GALACTONO 1,6 LACTONE 
690 1 0 |a POLYESTER 
690 1 0 |a SCANDIUM TRIFLATE 
690 1 0 |a TRIFLUOROMETHANESULFONIC ACID 
690 1 0 |a UNCLASSIFIED DRUG 
690 1 0 |a ARTICLE 
690 1 0 |a DEPROTECTION REACTION 
690 1 0 |a LACTONIZATION 
690 1 0 |a METHYLATION 
690 1 0 |a POLYMERIZATION 
690 1 0 |a PRIORITY JOURNAL 
690 1 0 |a SYNTHESIS 
690 1 0 |a HEXANOIC ACIDS 
690 1 0 |a LACTONES 
690 1 0 |a POLYESTERS 
690 1 0 |a SUGAR ACIDS 
690 1 0 |a TETRA 
700 1 |a Varela, O. 
773 0 |d 2006  |g v. 341  |h pp. 2973-2977  |k n. 18  |p Carbohydr. Res.  |x 00086215  |w (AR-BaUEN)CENRE-301  |t Carbohydrate Research 
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