Laboratoire d'Innovation Moléculaire et Applications (LIMA) , Université de Strasbourg/Université de Haute-Alsace/CNRS (UMR 7042), Equipe de Synthèse Organique et Molécules Bioactives (SYBIO), ECPM , 25 rue Becquerel , 67087 Strasbourg , France.
Org Lett. 2019 Sep 20;21(18):7262-7267. doi: 10.1021/acs.orglett.9b02496. Epub 2019 Sep 9.
We describe herein a convenient strategy for the construction of ,-glycoside building blocks via the intermediacy of tertiary pseudoanomeric radicals. Application of an iron-mediated hydrogen atom transfer/Michael-Giese coupling enables the anomeric quaternization of readily available -glycals with good to complete stereocontrol in the pyranose and furanose series. Carefully optimized conditions allow the use of challenging trisubstituted derivatives prone to undergo further elaboration to stable neoglycoconjugates. Preliminary results for direct -disaccharide synthesis are also discussed.
我们在此描述了一种通过叔伪糖基自由基中间体构建,-糖苷砌块的便捷策略。铁介导的氢原子转移/Michael-Giese 偶联反应的应用使得易于获得的 - 糖醛在吡喃糖和呋喃糖系列中具有良好至完全的立体选择性进行烯丙基季铵化。经过仔细优化的条件允许使用具有挑战性的三取代衍生物，这些衍生物容易进一步进行稳定的新糖缀合物的合成。我们还讨论了直接 - 二糖合成的初步结果。
