title: Stereospecific, High-Yielding, and Green Synthesis of β-Glycosyl Esters.
abstract: A new method of synthesizing β-glycosyl esters stereospecifically has been developed by treating O-benzyl-protected glycosyl chlorides with Cs2CO3, tetrabutylammomium bromide (TBAB), a carboxylic acid, water, and granular polytetrafluoroethylene (PTFE) at 80 °C under mechanical agitation. D-Glucosyl, D-xylosyl, and D-galactosyl chlorides and 20 carboxylic acids were used to demonstrate the scope of the reaction. Control experiments showed that the water and granular PTFE had indispensable roles. Water-soluble TBAB has been found to be as efficient as N-methyl-N,N,N-trioctyloctan-1-ammonium chloride (Aliquat 336) in the reactions. After scaling up to 5-12 g, all of the products were obtained quantitatively via simple filtration and no organic solvents or chromatography was needed for the entire process.
authors.affiliation: Department of Chemistry, School of Science, Tianjin University, Tianjin 300072, China.
authors.forename: Suliu
authors.initials: S
authors.lastname: Feng
authors.affiliation: Department of Chemistry, School of Science, Tianjin University, Tianjin 300072, China.
authors.forename: Chunbao
authors.initials: C
authors.lastname: Li
mesh_terms: D004952:Esters / Q000737:chemistry*; D006027:Glycosides / Q000737:chemistry*; D006031:Glycosylation; D055772:Green Chemistry Technology; D011138:Polytetrafluoroethylene / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D004952:Esters; D006027:Glycosides; D011138:Polytetrafluoroethylene
keywords: bioactive molecules; glycosylation; green chemistry; natural products; organic synthesis