Abstract: Taking D-glucose as material,2,3,4,6-Tetra-O-acetyl-α-D-glucopyranosyl bromide(Compound 2) and 2,3,4,6-Tetra-O-acetyl-α-D-glucopyranosyl trichloroacetimidate(Compound 4') were synthesized by α-D-acetobromoglucose method(Method A) and trichloroacetonitrile method(Method B),respectively.Compounds 2 and 4' were coupled with methylcyclopentenolone(MCP),then deacetylated to form MCP-β-D-glucopyranosides3-methyl-1-oxocyclopenta-2-en-2-yl-β-D-glucopyranoside(Compound 1) and 5-methyl-1-oxocyclopenta-2-en-2-yl-β-D-glucopyranoside(Compound 1'),respectively.The molecular structures of intermediates and final products were characterized by ¹H NMR and HRMS.The thermal pyrolysis of glucosides 1 and 1' was also studied,and the results indicated that:1) The compounds synthesized by the two methods were target products,Method A was better than Method B.2) The optimal conditions of Method A were the molar ratio of MCP to compound 2 1:1.2 and reacting at 35℃ for 5 hours,the yield of target product reached 82.0% and the total yield of reaction was 59.6%.3) Glucosides 1 and 1'were added into cigarettes separately,the glucosides pyrolyzed into MCP during smoking,and their transfer rates to mainstream cigarette smoke were 16.13% and 16.40%,respectively.