Alternating StereoregularHead,Tail–Tail,Head‐Poly(Alkylened‐Glucaramides) Derived from a Homologous Series of Symmetrical Diamido‐di‐d‐Glucaric Acid Monomers

Abstract

A method for the synthesis and purification of a homologous series of symmetrical diamido-diacids derived from D-glucaric acid and six alkylenediamines is described. Treating D-glucaro-6,3-lactone with an equimolar amount of lithium acetate dihydrate yielded lithium D-glucarate-6,3-lactone, which in turn was reacted with six alkylenediamines in dimethyl sulfoxide to give the target diamido-diacids. Six new alternating stereoregular polyamides, head, tailtail, head-poly(alkylene D-glucaramides), were then synthesized by simple polycondensation reactions between the activated diamido-diacids [6,6'-(N,N'-alkylene)-bis(D-glucaramid-1-oic acid)s] and the alkylenediamines. Number average molecular weights for the polyamides were estimated by 1 H NMR end group analysis. Models for the three-dimensional shape of these alternating stereoregular polymers were produced from a combination of 1 H NMR data, molecular modeling studies performed on D-glucaramide, and crystal structures of various acyclic D-glucaric acid derivatives.

Selective oxidation of uronic acids into aldaric acids over gold catalyst

“…S9 †). In heterogeneous catalysis, the apparent activation energy observed is the activation energy of the reaction modied by heat of adsorption DH ad of the reaction 19504 | RSC Adv., 2015, 5,[19502][19503][19504][19505][19506][19507] This journal is © The Royal Society of Chemistry 2015 species. 39 Accordingly, the activation energy of a reaction does not depend on the concentration of the reactants.…”

Synthetic Polymers from Sugar-Based Monomers

“…The physical properties of poly(butylene succinate) (PBS) were modified by the insertion of monocyclic acetals 2,3-di-Omethylene-L-threitol (8) and dimethyl ester of 2,3-di-Omethylene-L-tartaric acid (45) over the whole range of compositions, 40 and the corresponding copolymers had a random chemical microstructure (Scheme 6). Some of them showed higher glass-transition temperature (T g ) values, lower melting temperatures, and lower crystallinity compared with the parent PBS homopolyester.…”

Glycopolymeric inhibitors of β‐glucuronidase. III. Configurational effects of hydroxy groups in pendant glyco‐units in polymers upon inhibition of β‐glucuronidase

“…The development of macromolecular syntheses from renewable carbon resources and the circulation system of the macromolecules are essential for human life 1. Thus acidic saccharide derivatives such as aldaric, aldonic, and alduronic acids have also been in use as starting blocks, for biomedical and/or biodegradable polymeric materials 2–24…”