Highly Selective β-Mannosylations and β-Rhamnosylations Catalyzed by Bis-thiourea
Qiuhan Li, Samuel M. Levi, Eric N. Jacobsen
Abstract
pyranosylations employing easily accessible acetonide-protected donors. A wide variety of alcohol nucleophiles, including complex natural products, glycosides, and amino acids were β-mannosylated and β-rhamnosylated successfully using an operationally simple protocol under mild and neutral conditions. Less nucleophilic acceptors such as phenols were also glycosylated efficiently in excellent yields and with high β-selectivities.
Topics & Concepts
ChemistryNucleophileThioureaPhenolsCatalysisAlcoholOrganic chemistryAcetonideCombinatorial chemistryTriamcinolone acetonideSurgeryMedicineCarbohydrate Chemistry and SynthesisGlycosylation and Glycoproteins ResearchChemical Synthesis and Analysis