α-Selective Glucosylation Can Be Achieved with 6-<i>O</i>-<i>para</i>-Nitrobenzoyl Protection
Helle H. Trinderup, Line Juul-Madsen, Laura Press, Michael Madsen, Henrik H. Jensen
Abstract
A systematic study of the effect of various 6-O-acyl groups on anomeric selectivity in glucosylations with thioglycoside donors was conducted. All eight different esters were found to induce moderate-to-high α-selectivity in glucosylation with l-menthol with the best being 6-O-p-nitrobenzoyl. The effect appears to be general across various glucosyl acceptors, glucosyl donor types, and modes of activation. No evidence was found in favor of distal participation.
Topics & Concepts
SelectivityAnomerChemistryMentholStereochemistryMedicinal chemistryCombinatorial chemistryOrganic chemistryCatalysisCarbohydrate Chemistry and SynthesisSynthesis of Organic CompoundsEnzyme Catalysis and Immobilization