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

• Published in: Chemical & pharmaceutical bulletin Vol. 72; no. 4; pp. 408 - 412
• Main Authors: Kajimoto, Tetsuya, Du, Tianqi, Kaneko, Kimiyoshi, Matsushima, Yasuyuki, Miura, Tsuyoshi
• Format: Journal Article
• Language: English
• Published: Japan The Pharmaceutical Society of Japan 2024; Japan Science and Technology Agency
• Subjects: 1,4-dioxane; Alcohols; Borneol; Dioxanes - chemistry; Glucuronides - chemical synthesis; Glucuronides - chemistry; Glycosylation; Menthol; methyl 1,2,3,4-tetra-O-acetyl-β-D-glucuronate; Molecular Structure; solvent effect; Solvents - chemistry; Substrates; trimethylsilyl bis(trifluoromethanesulfonyl)imide (Tf2NTMS); β-D-glucuronidation; solvent effect; trimethylsilyl bis(trifluoromethanesulfonyl)imide (Tf2NTMS); β-D-glucuronidation; methyl 1,2,3,4-tetra-O-acetyl-β-D-glucuronate; 1,4-dioxane
• ISSN: 0009-2363; 1347-5223
• DOI: 10.1248/cpb.c24-00068

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.