title: New derivatives of D-mannaric and galactaric acids. Synthesis of a new stereoregular Nylon 66 analog from carbohydrate-based monomers having the D-manno configuration.
abstract: 2,3,4,5-Tetra-O-methyl-D-mannaric and galactaric acids and their bis(pentachlorophenyl) esters have been prepared as crystalline compounds, in good yields, from D-mannitol and galactitol, respectively. A new stereoregular polyamide, analogous to Nylon 66, has been prepared by polycondensation of bis(pentachlorophenyl) 2,3,4,5-tetra-O-methyl-D-mannarate with 1,6-diamino-1,6-dideoxy-2,3,4,5-tetra-O-methyl-D-mannitol dihydrochloride. The polymer has a M(w) of 31,100 with a polydispersity of 1.5 (GPC). It was highly hygroscopic and soluble in ethanol, acetone, dimethyl sulfoxide, N,N-dimethylformamide and chloroform, but only slightly soluble in water.
authors.affiliation: Departamento de Química Orgánica y Farmacéutica, Universidad de Sevilla, Spain.
authors.forename: Manuel
authors.initials: M
authors.lastname: Mancera
authors.forename: Isaac
authors.initials: I
authors.lastname: Roffé
authors.forename: Manuel
authors.initials: M
authors.lastname: Rivas
authors.forename: Juan A
authors.initials: JA
authors.lastname: Galbis
mesh_terms: D002236:Carbohydrate Conformation; D002241:Carbohydrates / Q000138:chemical synthesis / Q000737:chemistry; D004376:Galactitol / Q000031:analogs & derivatives / Q000138:chemical synthesis*; D008353:Mannitol / Q000031:analogs & derivatives / Q000138:chemical synthesis*; D008956:Models, Chemical; D009757:Nylons / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D002241:Carbohydrates; D009757:Nylons; D004376:Galactitol; D008353:Mannitol