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 with epsilon-caprolactone by ring-opening polymerization catalyzed by scandium triflate. The incorporation of the sugar comonomer into the polyester chain was about 10%.
Romero Zaliz
C Lorena
CL
CIHIDECAR-CONICET, Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Pabellón II, Ciudad Universitaria, 1428-Buenos Aires, Argentina.
Varela
Oscar
O
D002208:Caproates / Q000737:chemistry; D007783:Lactones / Q000737:chemistry; D011091:Polyesters / Q000138:chemical synthesis; D013400:Sugar Acids / Q000138:chemical synthesis / Q000737:chemistry*
D002208:Caproates; D007783:Lactones; D011091:Polyesters; D013400:Sugar Acids; C012991:galactonic acid; C007813:galactonolactone; C121056:caprolactone