School of Chemical Engineering and Technology, Tianjin University, 92 Weijin Road, Tianjin 300072, China.
J Org Chem. 2011 May 20;76(10):3654-63. doi: 10.1021/jo200440r. Epub 2011 Apr 13.
Clemoarmanoside A and Clemahexapetoside A, two novel cyclic dimers of 4-(glycosyloxy)benzoates containing the unusual d-allopyranose as one of the sugar units, were synthesized for the first time. The convenient synthetic approach was adapted to the assembly of the symmetrical trimeric, tetrameric, and pentameric congeners. The synthesis clarified the discrepancy in the NMR data reported for the natural products. X-ray diffraction analysis of Clemahexapetoside A revealed that it adopted an armchair conformation with two carbohydrate rings as the arms and two aromatic rings as the back and seat, respectively.
克莱莫马索苷 A 和克莱马六甲苷 A，这两种新型的 4-（糖氧基）苯甲酸酯的环状二聚体含有不常见的 D-吡喃葡萄糖作为糖单元之一，首次被合成。方便的合成方法适用于对称的三聚体、四聚体和五聚体同系物的组装。该合成方法澄清了天然产物报道的 NMR 数据中的差异。克莱马六甲苷 A 的 X 射线衍射分析表明，它采用了扶手椅构象，其中两个糖环作为臂，两个芳环分别作为背和座。
