Research On Synthesis Of Amino Acid Glucose Ester Derivatives

With the needs of sustainable development strategy, the chemical industry based on renewable materials has become an inevitable trend. Because of their superiority in abundant source, good chemical stability, biologicalactivity, non-toxic, using amino acid and sugar as raw materials to produce chemical products has great potential.Used as medicine, amino acid glucose esters have been shown to have antibacterial, antitumor, anti cancer effect; as the surface active agent, they have_better hydrophilicity and lipophilicity, safe, nontoxic and biodegradable.In this dissertation,32 new amino acid glucose ester compounds was synthesized using amino acid, glucose and fatty acyl chloride as raw materials in four steps including hydroxyl protection and Schotten-Baumann condensation reaction, Steglich estemfication reaction, hydrogenolysis debenzylation. The products of each step were characterized by IR,’HNMR and ES1-MS. On the basis of reported references, the reaction conditions of protect hydroxy reaction and acylation reaction were improved and optimized, the EDC1/DMAP [1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride/4-dimethyl-aminopyridine] catalytic condensation reaction, hydrogenolysis debenzylation reaction process conditions also explored and optimized. The optimal conditions of each reaction were confirmed depending on the experimental data:(1) In hydroxyl protection:the molar ratio 1:5.0:5.2 (methyl glucose:NaH:benzyl bromide), the reaction temperature 40℃. The Demethylation temperature is 85 ℃, two step overall yielding to 48.6%. (2) Schotten-Baumann condensation reaction:acetone-(sodium hydroxide solution) as solvent, the molar ratio 2:1 (amino acid:hloride), pH about 9, reaction temperature and time 25℃,3 h, the yield over 95%.(3) Steglich esterification:the molar ratio 1:1.2:1.4 (benzyl glucose:N-acyl amino acid:EDC1), the catalyst DMAP in an amount of 10% mass of glucose, the reaction temperature 28℃, yielding to 92.7%. (4)hydrogenolysis debenzylation reaction:5% Pd/C in an amount of 20%the mass fraction of reactants, solvent for methylene chloride-ethanol (volume ratio 1:1), the reaction temperature 35℃, yielding to 52.4%.The reaction of the substrate structure on reaction time and yield for esterification, hydrogenolysis debenzylation reaction also studied. As the growth of the alkyl chain of reactants, esterification and hydrogen release benzyl reaction time was grow, the esterification reaction yield basically remain unchanged, hydrogenolysis debenzylation reaction yield was reduced.