Kur'ianov V O, Tokarev M K, Chupakhina T A, Chirva V Ia
Bioorg Khim. 2011 Sep-Oct;37(5):672-8. doi: 10.1134/s1068162011050104.
The catalytic phase transfer reactions of 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-a-D-glucopyranosyl chloride with thiosubstituted 4-phenyl-5-R-thio-Delta2-1,2,4-triazolin-3-ones in solid alkali-organic solvent and in aqueous alkali-organic solvent were studied. The main products ofglucosaminilation reaction are the appropriate N-beta-glucosaminides. The effect of reaction conditions on the yield and composition of products formed was elucidated on the example of the reaction alpha-D-glucosaminyl chloride with 5-methylthio-4-phenyl-Delta2-1,2,4-triazolin-3-one. The optimal conditions of phase transfer glycosylation were established. N-1,2-trans-grycosidic bond formation was proved by 1H NMR and IR data as well as a comparison with spectral data obtained previously for the glycosides of similar structure.
研究了2-乙酰氨基-3,4,6-三-O-乙酰基-2-脱氧-α-D-吡喃葡萄糖基氯与硫代取代的4-苯基-5-R-硫代-Δ2-1,2,4-三唑啉-3-酮在固体碱-有机溶剂和碱水溶液-有机溶剂中的催化相转移反应。糖胺化反应的主要产物是相应的N-β-氨基葡萄糖苷。以α-D-氨基葡萄糖基氯与5-甲硫基-4-苯基-Δ2-1,2,4-三唑啉-3-酮的反应为例，阐明了反应条件对产物收率和组成的影响。确定了相转移糖基化的最佳条件。通过1H NMR和IR数据以及与先前获得的类似结构糖苷的光谱数据进行比较，证明了N-1,2-反式糖苷键的形成。
