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

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.

SUBMITTER: Geringer SA

PROVIDER: S-EPMC7656231 | biostudies-literature | 2020 Jul

REPOSITORIES: biostudies-literature

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

Geringer Scott A SA Mannino Michael P MP Bandara Mithila D MD Demchenko Alexei V AV

Organic & biomolecular chemistry 20200701 25

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 chemose ...[more]

PMID: 32608450

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