Study On Synthesis Of Two Methyl α-D-Glucopyranoside Esters And Their Application In Cigarette

The synthetic route for methyl 6-O-acetyl-2,3,4-tri-O-isobutyryl-α-D-Glucopyranoside by using enzymic catalytic technology combined with chemical synthetic technology was designed in the thesis. Systematical literatures searching about this project proved this synthetic route to be a new technology route.Experiment result showed the route have the advantage of high yield, simple operation and energy-saving. A new cigarette additive methyl 6-O-acetyl-2,3,4-tri-O-(3-methylvaleryl)-α-D-glucopyranoside was also synthesized in this thesis by the method which Chengzhifei (one member of our research group) had peformed in glucopyranose ester synthesis. Pyrolytic GC-MS analyses of the products showed that the two final products yielded isobutyric acid and 3-methylvaleric acid which were important flavor compounds for tobacco smoke at high temperature.The conversion rate of the products was mensurated by smoke analysis after adding the products into cigarette. The optimum dosage of the products was determined by sensory evaluation.The main content of the thesis including:1. The synthesis of methyl 6-O-acetyl-2,3,4-tri-O-isobutyryl-α-D-glucopyranosideMethyl α-D-glucopyranoside was esterified to give methyl 2,3,4,6-tetra-O-isobutyryl-α-D-Glucopyranoside(I). After enzyme-catalyzed regioselective deacylation of I, methyl 2,3,4-tri-O-isobutyryl--α-D-gluco-pyranoside(II) was obtained. The target product methyl 6-O-acetyl-2,3,4-tri-Oiso-butyryl-α-D-glucopyranoside was prepared through acetylation of II, the total yield was 61.3%.2. The synthesis of methyl 6-O-acetyl-2,3,4-tri-O-(3-methylvaleryl)-α- D-glucopyranosideMethyl 6-Otrityl-α-D-glucopyranoside(III) was selectively synthesized began with methyl α-D-glucopyranoside. Then, III was esterified to give methyl 2,3,4-tri-O-(3-methylval-eryl)-6-O-trityl-α-D-glucopyranoside(VI).Subsequently, through detritylation of the VI, methyl 2,3,4-tri-O-(3-methylvaleryl)-α-D-glucopyranoside(V) was obtained. The target product methyl 6-O-acetyl-2,3,4-tri-O-(3-methylvaleryl)-α-D-glucopyranoside was prepared thorugh acetylation of V, the total yield was 27%.3. Study on PGC analysis of the final products.By Pyrolytic GC-MS analyses of the two products at 850℃, the result showed that the...