Iodoetherification of Isosorbide‐Derived Glycals: Access to a Variety of O‐Alkyl or O‐Aryl Isosorbide Derivatives
Iodoetherification of Isosorbide‐Derived Glycals: Access to a Variety of O‐Alkyl or O‐Aryl Isosorbide Derivatives
复制标题
异山梨醇衍生的二醇的碘醚化：获得各种 O-烷基或 O-芳基异山梨醇衍生物
DOI：
10.1002/ejoc.201201547
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发表时间：
2013
影响因子：
2.8
通讯作者：
J. Aubry
中科院分区：
文献类型：
--
作者：
C. Berini;A. Lavergne;V. Molinier;F. Capet;E. Deniau;J. Aubry
以异山梨醇为原料合成了一系列O-烷基化或O-芳基化的β-碘醚。异山梨醇是通过官能化和/或取代的各种有价值的衍生物的有竞争力的起始材料，因为它是由山梨醇以工业规模生产的可再生和碳中性材料。关键步骤是在N-碘代琥珀酰亚胺存在下，异山梨醇衍生的糖与各种含氧亲核试剂的碘醚化反应。以良好的产率得到反式碘醚和乙酸酯，除去碘化物得到异山梨醇衍生物。这种新方法的有用性说明了由具有异山梨醇作为亲水基团的二聚体的表面活性剂的合成和由结构上不寻常的双环脱水碳水化合物的制备。
A set of O-alkylated or O-arylated β-iodo ethers has been synthesized from isosorbide. Isosorbide is a competitive starting material for various valuable derivatives by functionalization and/or substitution since it is a renewable and carbon neutral material that is produced on an industrial scale from sorbitol. The key step was the iodoetherification of isosorbide-derived glycals with a variety of oxygenated nucleophiles in the presence of N-iodosuccinimide. trans-Iodo ethers and acetate were obtained in good yields and the removal of iodide affords isosorbide derivatives. The usefulness of this new approach is illustrated by the synthesis of a surfactant having a dimer of isosorbide as hydrophilic group and by the preparation of a structurally unusual bicyclic anhydro carbohydrate.