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 Mw 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.