Open AccessPicoloyl protecting group in synthesis: focus on a highly chemoselective catalytic removal
Author(s) -
Scott A. Geringer,
Michael P. Mannino,
Mithila D. Bandara,
Alexei V. Demchenko
Publication year - 2020
Publication title -
organic and biomolecular chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.923
H-Index - 146
eISSN - 1477-0539
pISSN - 1477-0520
DOI - 10.1039/d0ob00803f
Subject(s) - chemistry , catalysis , chemoselectivity , protecting group , combinatorial chemistry , group (periodic table) , organic chemistry , alkyl
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.