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

Chem Pharm Bull (Tokyo). 2024;72(4):408-412. doi: 10.1248/cpb.c24-00068.

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.

Keywords: 1,4-dioxane; methyl 1,2,3,4-tetra-O-acetyl-β-D-glucuronate; solvent effect; trimethylsilyl bis(trifluoromethanesulfonyl)imide (Tf2NTMS); β-D-glucuronidation.

MeSH terms

  • Dioxanes* / chemistry
  • Glucuronides / chemical synthesis
  • Glucuronides / chemistry
  • Glycosylation
  • Molecular Structure
  • Solvents* / chemistry

Substances

  • Dioxanes
  • 1,4-dioxane
  • Solvents
  • Glucuronides