Abstract: To improve the synthesis yield of furfuryl alcohol-β-D-glucoside in smoke, synthesis conditions and pyrolysis products were investigated and the transfer rate of furfuryl alcohol to the particulate phase of mainstream cigarette smoke was measured. The results showed that: 1) Furfuryl alcohol and acetyl bromide-α-D-glucose underwent glycosylation reaction under the catalysis of Ag₂CO₃ supported on silica gel and NaOH solid as acid binder to obtain furfuryl alcohol-2, 3, 4, 6-tetra-O-acetyl-β-D-glucoside. The optimized yield of furfuryl alcohol-2, 3, 4, 6-tetra-O-acetyl-β-D-glucoside was 45.9%. The intermediate furfuryl alcohol-2, 3, 4, 6-tetra-O-acetyl-β-D-glucoside was deacetylated to obtain furfuryl alcohol-β-D-glucoside with a yield of 90.1%. The structures of the intermediates and the final products were confirmed by ¹H NMR, ¹³C NMR, FTIR and HRMS. 2) At different temperatures, the main cleavage product of furfuryl alcohol-β-D-glucoside was furfuryl alcohol. 3) Furfuryl alcohol-β-D-glucoside released furfuryl alcohol during cigarette smoking, and the transfer rate of furfuryl alcohol to the particulate phase of mainstream cigarette smoke was 0.68%.