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

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

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Picoloyl 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) - tetrasaccharide , glycan , catalysis , protecting group , chemistry , group (periodic table) , focus (optics) , organic chemistry , combinatorial chemistry , biochemistry , polysaccharide , physics , glycoprotein , alkyl , optics

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.

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