Scott A. Geringer, Michael P. Mannino, Mithila D. Bandara and Alexei V. Demchenko
Org. Biomol. Chem., 2020,18, 4863-4871
DOI:
10.1039/D0OB00803F,
Paper
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.