Effect of 1,4-Dioxane Solvent on β-Glucuronidation Using Methyl 1,2,3,4-Tetra-O-acetyl-β-D-glucuronate as the Glycosyl Donor.

IF 17.7 1区化学 Q1 CHEMISTRY, MULTIDISCIPLINARY Accounts of Chemical Research Pub Date : 2024-04-25 DOI:10.1248/cpb.c24-00068

Tetsuya Kajimoto, Tianqi Du, Kimiyoshi Kaneko, Yasuyuki Matsushima, Tsuyoshi Miura

引用次数: 0

Abstract

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.

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以 1,2,3,4-O-四乙酰基-β-D-葡萄糖醛酸甲酯为糖基供体，1,4-二氧六环溶剂对β-葡萄糖醛酸化作用的影响

使用市售的 1，2，3，4-四-O-乙酰基-β-D-葡萄糖醛酸甲酯作为糖基供体，三甲基硅基双（三氟甲烷磺酰）亚胺（Tf2NTMS）（0.5 当量）作为活化剂，在 60 °C、1,4-二氧六环中进行反应，得到的产物收率适中。当使用胆甾醇、(+)-冰片醇和 2-金刚烷醇作为受体底物时，加入 MS4A 可提高 D-葡萄糖醛酸的 β : α 比率。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Accounts of Chemical Research 化学-化学综合

CiteScore

31.40

自引率

1.10%

发文量

312

审稿时长

2 months

期刊介绍： Accounts of Chemical Research presents short, concise and critical articles offering easy-to-read overviews of basic research and applications in all areas of chemistry and biochemistry. These short reviews focus on research from the author’s own laboratory and are designed to teach the reader about a research project. In addition, Accounts of Chemical Research publishes commentaries that give an informed opinion on a current research problem. Special Issues online are devoted to a single topic of unusual activity and significance. Accounts of Chemical Research replaces the traditional article abstract with an article "Conspectus." These entries synopsize the research affording the reader a closer look at the content and significance of an article. Through this provision of a more detailed description of the article contents, the Conspectus enhances the article's discoverability by search engines and the exposure for the research.