Novel D- glucose Based Glycomonomers Synthesis and Characterization

In the last decade, carbohydrates have attracted great attention as renewable resources for the chemical industry. Carbohydrates are abundantly found in nature in the form of monomers, oligomers and polymers, or as components of biopolymers and other naturally occurring substances. As natural products, they play important roles in conferring certain physical, chemical, and biological properties to their carrier molecules.The synthesis of this particular carbohydrate glycomonomer is part of our work to obtain biodegradable polymers. Our current paper describes the synthesis and characterization of a novel carbohydrate glycomonomer starting from D-glucose, in several synthesis steps, that involve the protection/deprotection of the D-glucose ring via acetylation, tritylation, then selective deprotection of the aromaticaliphatic protective group, in order to obtain 1,2,3,4-tetra-O-acetyl6-O-allyl-β-D-glucopyranose. The glycomonomer was then obtained by the allylation in drastic conditions of 1,2,3,4-tetra-O-acetyl-6-Oallyl-β-D-glucopyranose with allylic alcohol in the presence of stannic chloride, in methylene chloride, at room temperature. The proposed structure of the glycomonomer, 2,3,4-tri-O-acetyl-1,6-diO-allyl-β-D-glucopyranose, was confirmed by FTIR, NMR and HPLC-MS spectrometry. This glycomonomer will be further submitted to copolymerization with certain acrylic or methacrylic monomers in order to obtain competitive plastic materials for applications in the biomedical field. Keywords—allylation, D-glucose, glycomonomer, trityl chloride M. S. Mazăre is a PhD student at the “Politehnica” University of Timişoara, Faculty of Industrial Chemistry and Environmental Engineering, C. Telbisz 6, 300001, Timişoara, Romania (corresponding author: phone: +40256404225, fax: +40256403060, email: [email protected]). L. M. Ştefan is a PhD student at the “Politehnica” University of Timişoara, Faculty of Industrial Chemistry and Environmental Engineering, C. Telbisz 6, 300001, Timişoara, Romania (email: [email protected]). A. M. Pană is a postdoctoral research with the “Gheorghe Asachi” Technical University of Iaşi, Faculty of Chemical Engineering and Environmental Protection (email: [email protected]). M. Silion is with the “Petru Poni” Institute of Macromolecular Chemistry, Aleea Gr. Ghica Vodă 41 A, Iaşi (email: [email protected]). M. Bălan is with the “Petru Poni” Institute of Macromolecular Chemistry, Aleea Gr. Ghica Vodă 41 A, Iaşi (email:[email protected]). G. Bandur is Professor of Department of Organic Chemical Tehnology of “Politehnica” University of Timişoara, Faculty of Industrial Chemistry and Environmental Engineering (email: [email protected]). L. M. Rusnac is the Dean of the Faculty of Industrial Chemistry and Environmental Engineering of “Politehnica” University of Timişoara, and a professor of Department of Organic Chemical Tehnology of Faculty of Industrial Chemistry and Environmental Engineering, email: [email protected]).