Picoloyl protecting group in synthesis: focus on a highly chemoselective catalytic removal
Scott A. Geringer, Michael P. Mannino, Mithila D. Bandara, Alexei V. Demchenko
Abstract
The picoloyl ester (Pico) has proven to be a versatile protecting group in carbohydrate chemistry. It can be used for the purpose of stereocontrolling glycosylations via an H-bond-mediated Aglycone Delivery (HAD) method. It can also be used as a temporary protecting group that can be efficiently introduced and chemoselectively cleaved in the presence of practically all other common protecting groups used in synthesis. Herein, we will describe a new method for rapid, catalytic, and highly chemoselective removal of the picoloyl group using inexpensive copper(ii) or iron(iii) salts.
Topics & Concepts
TetrasaccharideGlycanCatalysisProtecting groupChemistryGroup (periodic table)Focus (optics)Organic chemistryCombinatorial chemistryBiochemistryPolysaccharidePhysicsGlycoproteinOpticsAlkylCarbohydrate Chemistry and SynthesisGlycosylation and Glycoproteins ResearchChemical Synthesis and Analysis