To improve and optimize the synthetic process of the glycosylation, 2,3,4,6-O-Tetraacetyl-α-D-glucopyranosyl bromide(Ⅲ) was prepared from D-glucose via acetylation, bromination. The 2,3,4-trimethoxybenzaldhyde could provide 2-hydroxy-3,4-dimeth-oxybenzaldhyde(Ⅳ) selectively by using AlCl3 . Then, 3,4-dimethoxybenzaldhyde-2-O-β-D-acety -glucoside(Ⅴ) and 3,4-dimethoxybenzaldhyde-2-O-β-D-glucoside (Ⅵ) were obtained from Ⅳ and Ⅲ by glycosylation, hydrolysis respectively. The results indicated that the yield of O-glycosyl (Ⅴ) could reach 78.9%, while anhydrous K2CO3 and tetrabutyl ammonium bromide were used, the application of the methanol and anhydrous K2CO3 was the preferred hydrolysis system of Ⅴ. The structures of the synthetic compounds were confirmed by 1HNMR, 13CNMR, IR and MS spectrum analysis.