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

IF 1.5 4区医学 Q4 CHEMISTRY, MEDICINAL

Chemical & pharmaceutical bulletin Pub Date : 2024-04-25 DOI:10.1248/cpb.c24-00068

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

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引用次数: 0

摘要

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。

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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.

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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来源期刊

Chemical & pharmaceutical bulletin 医学-化学综合

CiteScore

3.20

自引率

5.90%

发文量

132

审稿时长

1.7 months

期刊介绍： The CPB covers various chemical topics in the pharmaceutical and health sciences fields dealing with biologically active compounds, natural products, and medicines, while BPB deals with a wide range of biological topics in the pharmaceutical and health sciences fields including scientific research from basic to clinical studies. For details of their respective scopes, please refer to the submission topic categories below. Topics: Organic chemistry In silico science Inorganic chemistry Pharmacognosy Health statistics Forensic science Biochemistry Pharmacology Pharmaceutical care and science Medicinal chemistry Analytical chemistry Physical pharmacy Natural product chemistry Toxicology Environmental science Molecular and cellular biology Biopharmacy and pharmacokinetics Pharmaceutical education Chemical biology Physical chemistry Pharmaceutical engineering Epidemiology Hygiene Regulatory science Immunology and microbiology Clinical pharmacy Miscellaneous.