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.
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.
Mancera
Manuel
M
Departamento de Química Orgánica y Farmacéutica, Universidad de Sevilla, Spain.
Roffé
Isaac
I
Rivas
Manuel
M
Galbis
Juan A
JA
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
D002241:Carbohydrates; D009757:Nylons; D004376:Galactitol; D008353:Mannitol