Effect of 1,4-Dioxane Solvent on β-Glucuronidation Using Methyl 1,2,3,4-Tetra-<i>O</i>-acetyl-β-D-glucuronate as the Glycosyl Donor
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- Kajimoto Tetsuya
- College of Pharmaceutical Sciences, Ritsumeikan University
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- Du Tianqi
- College of Pharmaceutical Sciences, Ritsumeikan University
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- Kaneko Kimiyoshi
- Research Organization of Science and Technology, Ritsumeikan University
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- Matsushima Yasuyuki
- School of Pharmacy, Tokyo University of Pharmacy and Life Sciences
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- Miura Tsuyoshi
- School of Pharmacy, Tokyo University of Pharmacy and Life Sciences
抄録
<p>A facile and selective β-D-glucuronidation of alcohols, such as (−)-menthol, cholestanol, (+)- and (−)-borneols, and 2-adamantanol, using commercially available methyl 1,2,3,4-tetra-O-acetyl-β-D-glucuronate as the glycosyl donor and trimethylsilyl bis(trifluoromethanesulfonyl)imide (Tf2NTMS) (0.5 equivalent) as the activator in 1,4-dioxane at 60 °C gave products in moderate yields. The addition of MS4A increased the β : α ratios of D-glucuronides when cholestanol, (+)-borneol, and 2-adamantanol were used as the acceptor substrate.</p>
収録刊行物
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- ＣＨＥＭＩＣＡＬ ＆ ＰＨＡＲＭＡＣＥＵＴＩＣＡＬ ＢＵＬＬＥＴＩＮ
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ＣＨＥＭＩＣＡＬ ＆ ＰＨＡＲＭＡＣＥＵＴＩＣＡＬ ＢＵＬＬＥＴＩＮ 72 (4), 408-412, 2024-04-25
公益社団法人 日本薬学会