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Issue 25, 2020
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Picoloyl protecting group in synthesis: focus on a highly chemoselective catalytic removal

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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.

Graphical abstract: Picoloyl protecting group in synthesis: focus on a highly chemoselective catalytic removal

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Supplementary files

Article information


Submitted
17 Apr 2020
Accepted
05 Jun 2020
First published
10 Jun 2020

Org. Biomol. Chem., 2020,18, 4863-4871
Article type
Paper

Picoloyl protecting group in synthesis: focus on a highly chemoselective catalytic removal

S. A. Geringer, M. P. Mannino, M. D. Bandara and A. V. Demchenko, Org. Biomol. Chem., 2020, 18, 4863
DOI: 10.1039/D0OB00803F

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