V.I. Vernadsky Crimean Federal University, Vernadsky Ave., 4, 295007, Simferopol, Russian Federation.
N.D. Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences, Leninsky Prosp., 47, 119991, Moscow, Russian Federation.
Carbohydr Res. 2021 Jan;499:108230. doi: 10.1016/j.carres.2020.108230. Epub 2020 Dec 29.
The formation of macrocyclic pseudo-tetrasaccharide derivative of d-glucosamine as a result of the acid-catalyzed reaction between 2-methyl- and 2-(2,2,2-trichloroethoxy)-substituted oxazoline derivatives of sugars was discovered. The structure of the obtained product was determined using NMR spectroscopy and mass spectrometry. An explanation of the obtained results based on the mechanism of the reaction of electrophilic polymerization of 2-substituted glyco-[2,1-d]-2-oxazolines and the principle of hard and soft acids and bases (HSAB) was proposed.
研究发现，在糖的 2-甲基和 2-(2,2,2-三氯乙氧基）取代恶唑啉衍生物在酸催化下反应，形成了葡糖胺的大环假四糖衍生物。利用核磁共振光谱和质谱法确定了所得到的产物的结构。根据 2-取代的糖[2,1-d]-2-恶唑啉的亲电聚合反应机理和软硬酸碱原理（HSAB）提出了对所得到的结果的解释。
