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  

Synthesis of 3,5-dideoxy-6-O-triphenlmethyl-1,2-O-isopropylidene-α-D-glucofuranose

作　　者：姜宇华[1] 安乔[1] 方志杰[1] 郑保辉[1] 丰巍伟[1] 

机构地区：[1]南京理工大学化工学院,江苏南京210094

出　　处：《化学研究与应用》2011年第3期327-331,共5页Chemical Research and Application

摘　　要：以葡萄糖为原料合成35,-脱氧-6-O-三苯甲基-12,-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PPh3I、2和咪唑的作用下得到构型翻转的碘代产物,接着在LiAlH4或者Pd/C-H2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1H NMR表征。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.

关 键 词：脱羟基反应 碘代反应 机理 空间位阻 合成 

分 类 号：O624.6[理学—有机化学]