Abstract: D-Glucoheptulose was synthesized by iodomethylation using D-glucolactone as the starting material. Firstly, 2,3,4,6-tetra-O-trimethylsilanyl-D-glucolactone was prepared from D-glucolactone under the catalyst of N-methylmorpholine, with a yield of 95％. Secondly, 2,7-dehydrate-β-D-glucoheptulopyranose was synthesized by addition of iodomethyl lithium generated from CH2I2/n-BuLi to the carbonyl group of lactone, and then hydrolysis under basic conditions, with a yield of 62％. Finally, D-glucoheptulose was prepared by hydrolysis under acidic conditions, with a yield of 90％(total yield 53％). The acetylated products of the target compound D-glucoheptulose and the key intermediate 2,7-dehydrate-β-D-glucoheptulopyranose were characterized by NMR.

Key words: iodomethylation, D-glucoheptulose, synthesis