首页> 中文期刊> 《化学研究与应用》 >3,5-脱氧-6-O-三苯甲基-1,2-O-异丙叉基-α-D-呋喃葡萄糖的合成研究

3,5-脱氧-6-O-三苯甲基-1,2-O-异丙叉基-α-D-呋喃葡萄糖的合成研究

         

摘要

3,5-dideoxy-6-O-triphenlmethyl-1,2-O-isopropylidene-α-D-glucofuranose was synthesized from D-glucose by seven steps in the total yield of 16%. The key step of the synthetic route was dehydroxylation reaction: hydroxyl-group in glucose derivatives was transformed into iodo-group with inversion of configuration on treatment with PPh3,I2 and imidazole, then was deiodination with LiAlH4 or Pd/C-H2. The mechanism of iodination and the influencing factors were studied. The structures of the compounds were characterized by 1H NMR.%以葡萄糖为原料合成3,5-脱氧-6-O-三苯甲基-1,2-O-异丙叉基-α-D-呋喃葡萄糖,总产率16%.该路线的关键步骤是脱羟基反应:葡萄糖衍生物首先在PPh<,3>、I<,2>和咪唑的作用下得到构型翻转的碘代产物,接着在LiAlH<,4>或者Pd/C-H<,2>:条件下进行脱碘反应.研究了碘代反应机理和影响因素,化合物的结构经<'1>H NMR表征.

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