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

Scott A. Geringer; Michael P. Mannino; Mithila D. Bandara; Alexei Demchenko

doi:10.1039/D0OB00803F

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

Scott A. Geringer, Michael P. Mannino, Mithila D. Bandara, Alexei Demchenko

University of Missouri-St. Louis

Research output: Contribution to journal › Article › peer-review

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.

Original language	American English
Journal	Organic & Biomolecular Chemistry
DOIs	https://doi.org/10.1039/D0OB00803F
State	Published - 2020

Disciplines

Biochemistry, Biophysics, and Structural Biology

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10.1039/D0OB00803FLicense: Unspecified

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title = "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. ",

author = "Geringer, {Scott A.} and Mannino, {Michael P.} and Bandara, {Mithila D.} and Alexei Demchenko",

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doi = "10.1039/D0OB00803F",

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T1 - Picoloyl protecting group in synthesis: focus on a highly chemoselective catalytic removal

AU - Geringer, Scott A.

AU - Mannino, Michael P.

AU - Bandara, Mithila D.

AU - Demchenko, Alexei

N1 - 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 a

PY - 2020

Y1 - 2020

N2 - 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.

AB - 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.

UR - https://doi.org/10.1039/D0OB00803F

U2 - 10.1039/D0OB00803F

DO - 10.1039/D0OB00803F

M3 - Article

JO - Organic & Biomolecular Chemistry

JF - Organic & Biomolecular Chemistry

ER -

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

Abstract

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