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Specific Features of Phase Transfer Catalytic Glycosylation of 2-Mercaptobenzimidazole
Russian Journal of Bioorganic Chemistry ( IF 1.1 ) Pub Date : 2020-11-01 , DOI: 10.1134/s1068162020060047
T. A. Chupakhina , V. O. Kur’yanov

Abstract The reaction of 2-acetamido-3,4,6-tri- O -acetyl-2-deoxy-α-D-glucopyranosyl chloride with 2‑mercaptobenzimidazole under conditions of the phase transfer catalysis was studied and specific features of the phase transfer process were evaluated. It was found that the corresponding N - and S -β-D-glucosaminides were the major glucosaminylation products. Glucosaminylation of 2-mercaptobenzimidazole in an anhydrous methylene chloride–sodium hydride phase transfer catalytic system was shown to proceed regiospecifically. The structures of the synthesized compounds were characterized using 1 H NMR spectroscopy and mass spectrometry.

中文翻译:

2-巯基苯并咪唑相转移催化糖基化的特性

摘要 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2-巯基苯并咪唑在相转移催化条件下的反应及其相转移的特点。过程进行了评价。发现相应的N-和S-β-D-氨基葡萄糖是主要的氨基葡萄糖化产物。2-巯基苯并咪唑在无水二氯甲烷-氢化钠相转移催化体系中的氨基葡萄糖化显示出区域特异性。合成化合物的结构使用 1 H NMR 光谱和质谱进行表征。
更新日期:2020-11-01
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