Controlled Garegg Conditions for Selective Iodination on Pyranose Templates
Controlled Garegg Conditions for Selective Iodination on Pyranose Templates
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DOI：
10.1002/ejoc.201001325
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发表时间：
2011-04-01
影响因子：
2.8
通讯作者：
Tatibouet, Arnaud
中科院分区：
文献类型：
--
作者：
Simao, Ana-Catarina;Silva, Sandrina;Tatibouet, Arnaud
在受控的Garegg条件下，对位于吡喃糖模板上的邻位二醇和邻接三醇进行区域和立体选择性碘标记。分别在C-5或C-4位选择性地对基于β-D-果糖或吡喃糖基的二醇进行碘化，得到L-索尔波或D-塔加托碘海合物。相比之下，相关的三醇只在C-5处进行了选择性碘化。将该方法应用于D-葡萄糖苷和D-半乳糖吡喃糖苷，分别在C-3或C-4选择性地进行碘化，得到D-别氨基或D-葡萄糖基碘氢化物。
Regio- and stereoselective iodinations under controlled Garegg conditions were performed on vicinal diols and contiguous triols located on pyranose templates. beta-D-Fructo- or psicopyranose-based diols were selectively iodinated at C-5 or C-4, respectively, to afford the L-sorbo or D-tagato iodohydrins. In contrast, the related triols only underwent selective iodination at C-5. Application of the process to D-glucoand D-galactopyranosides resulted in selective iodination at C-3 or C-4, respectively, to afford the D-allo or D-gluco iodohydrins.