Abstract: To improve the synthetic process of glycosylation, 2, 3, 4, 6-tetra-O-acetyl-α-D-glucopyranosyl bromide (Ⅱ) was firstly synthesized from D-glucose. Then, a glycosylation reaction between compounds Ⅱ and maltol (I) led to maltol-2, 3, 4, 6-tetra-O-acetyl-β-D-glucoside (Ⅲ) by phase transfer catalysis method and Koenigs-Knorr method, respectively. Finally, the target compound maltol-β-D-glucoside (Ⅳ) was obtained by hydrolysis of compound Ⅲ. These compounds were confirmed by 1HNMR, 13CNMR, IR and HRMS. The effects of pyrolysis and aroma evaluation of target glycoside Ⅳ were studied. The results indicated that the compound Ⅲ synthesized by the two above-mentioned methods was target product, the phase transfer catalysis method was better than Koenigs-Knorr method. The optimal conditions for the preparation of compound Ⅲ by phase transfer catalysis method were as follows: acetone was used as the solvent, anhydrous potassium carbonate was used as acid binding agent, and tetrabutyl ammonium bromide (TBAB) was used as phase transfer catalyst, n (maltol): n (2, 3, 4, 6-tetra-O-acetyl-α-D-glucopyranosyl bromide)=1:1.2, reaction at room temperature for 4 h. Under these optimal conditions, the yield of compound Ⅲ reached 75.6%. Hydrolysis of compound III to compound IV in sodium methoxide/methanol system. The target glycoside Ⅳ can release characteristic flavor components such as maltol by pyrolysis, and can be added to cigarettes to improve the aroma quality.