Abstract: Soy sauce ketone -2,3,4,6-tetra-O-acetyl-β-D-glucoside (Ⅲ) and soy sauce ketone-β-D-glucoside (Ⅳ) was obtained by a glycosylation reaction between 2, 3, 4, 6-tetra-O-acetyl-α-D-glucopyranosyl bromide (Ⅰ) and Soy sauce ketone (Ⅱ). The process of synthesizing glycoside Ⅲ was explored silver salt method and phase transfer catalysis method. The structures of the intermediates and products were confirmed by 1HNMR, 13CNMR, IR and HRMS. Glycoside Ⅳ was added into cigarettes to determine its transfer rate in cigarette mainstream smoke. The results show that both methods can obtain glycoside Ⅲ, and the phase transfer catalysis method is better than Koenigs-Knorr method. The reaction conditions of phase transfer catalysis were as follows: tetrabutylammonium bromide (TBAB) as catalyst, anhydrous potassium carbonate as acid binding agent, dichloromethane as solvent, n (acetyl bromide-α-D-glucose): n (soy sauce ketone) =1.2:1.0, reaction at room temperature for 8 hours, and the yield of glycoside Ⅲ was 44.5%. The acetyl group of glycoside Ⅲ was removed in the sodium methoxide/methanol system to obtain the target glycoside Ⅳ in 88.0% yield. Glucoside Ⅳwas added into cigarettes, the glucoside pyrolyzed into soy sauce ketone during smoking, and its transfer rate to mainstream cigarette smoke was 3.1%.