Sosnowska Anna, Chojnacki Jarosław, Samaszko-Fiertek Justyna, Madaj Janusz, Dmochowska Barbara
Faculty of Chemistry, University of Gdansk, Wita Stwosza 63, 80-308 Gdansk, Poland.
Department of Inorganic Chemistry, GdańskTech, G. Narutowicza 11/12, 80-233 Gdansk, Poland.
Molecules. 2025 Jan 13;30(2):287. doi: 10.3390/molecules30020287.
γ- and δ-lactones were formed by bromine oxidation of commercially available D-lyxose, as confirmed by IR analysis. The former was isolated, and its structure was confirmed by NMR spectra and X-ray analysis. In this structure, the presence of both intermolecular and intramolecular hydrogen bonds was found. Intermolecular interactions in the crystal were illustrated using the Hirshfeld surfaces. Due to steric reasons, 3,5--isopropylidene-d-lyxono-1,4-lactone was formed, which in a further step led to the formation of a 2--tosyl derivative. Its structure was confirmed by X-ray diffraction analysis. The additional ring of the -isopropylidene derivative caused the lactone ring to change conformation to . In the crystal structure of this compound, only C-H⸱⸱⸱O intermolecular interactions were present, as confirmed by the Hirshfeld surface analysis.
通过红外分析证实，市售的D - 来苏糖经溴氧化形成了γ - 和δ - 内酯。分离出了前者，并通过核磁共振光谱和X射线分析确定了其结构。在该结构中，发现了分子间和分子内氢键的存在。使用Hirshfeld表面展示了晶体中的分子间相互作用。由于空间位阻原因，形成了3,5 - 异亚丙基 - D - 来苏糖 - 1,4 - 内酯，其在进一步反应中生成了2 - 对甲苯磺酰基衍生物。通过X射线衍射分析确定了其结构。异亚丙基衍生物的额外环使内酯环构象转变为 。在该化合物的晶体结构中，如Hirshfeld表面分析所证实的，仅存在C - H···O分子间相互作用。
