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Citation: SHI Mei, FANG Zhijie. Application of Iodomethylation to Synthesis of D-Glucoheptulose[J]. Chinese Journal of Applied Chemistry, ;2012, 29(3): 266-269. doi: 10.3724/SP.J.1095.2012.00138 shu

Application of Iodomethylation to Synthesis of D-Glucoheptulose

SHI Mei ^a ,
FANG Zhijie ^b,,

1.
a Department of Chemistry, Nanjing Xiaozhuang University, Nanjing 211171, China;
2.
b School of Chemical Engineering, Nanjing University of Science and Technology, Nanjing 210094, China

Corresponding author: FANG Zhijie,
Received Date: 6 April 2011
Available Online: 3 June 2011

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.
- iodomethylation,
- D-glucoheptulose,
- synthesis
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