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Literature DB >> 32608450

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

Scott A Geringer¹, Michael P Mannino¹, Mithila D Bandara¹, Alexei V Demchenko¹.

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.

Entities: CellLine Chemical Disease Gene Species

Year: 2020 PMID： 32608450 PMCID： PMC7656231 DOI： 10.1039/d0ob00803f

Source DB: PubMed Journal: Org Biomol Chem ISSN： 1477-0520 Impact factor: 3.876

35 in total

1. Chemical Synthesis of Modified Hyaluronic Acid Disaccharides.

Authors: Marco Mende; Martin Nieger; Stefan Bräse
Journal: Chemistry Date: 2017-05-23 Impact factor: 5.236

2. Assistance of the C-7,8-Picoloyl Moiety for Directing the Glycosyl Acceptors into the α-Orientation for the Glycosylation of Sialyl Donors.

Authors: Yu-Fa Wu; Yow-Fu Tsai
Journal: Org Lett Date: 2017-07-28 Impact factor: 6.005

3. Active Site Mapping of Xylan-Deconstructing Enzymes with Arabinoxylan Oligosaccharides Produced by Automated Glycan Assembly.

Authors: Deborah Senf; Colin Ruprecht; Goswinus H M de Kruijff; Sebastian O Simonetti; Frank Schuhmacher; Peter H Seeberger; Fabian Pfrengle
Journal: Chemistry Date: 2017-02-08 Impact factor: 5.236

4. Synthesis of β-Glucosides with 3-O-Picoloyl-Protected Glycosyl Donors in the Presence of Excess Triflic Acid: A Mechanistic Study.

Authors: Michael P Mannino; Alexei V Demchenko
Journal: Chemistry Date: 2020-01-31 Impact factor: 5.236

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

1. Chemical Synthesis of Modified Hyaluronic Acid Disaccharides.

2. Assistance of the C-7,8-Picoloyl Moiety for Directing the Glycosyl Acceptors into the α-Orientation for the Glycosylation of Sialyl Donors.

3. Active Site Mapping of Xylan-Deconstructing Enzymes with Arabinoxylan Oligosaccharides Produced by Automated Glycan Assembly.

4. Synthesis of β-Glucosides with 3-O-Picoloyl-Protected Glycosyl Donors in the Presence of Excess Triflic Acid: A Mechanistic Study.

5. The chemical synthesis of human milk oligosaccharides: Lacto-N-neotetraose (Galβ1→4GlcNAcβ1→3Galβ1→4Glc).

6. C6 picoloyl protection: a remote stereodirecting group for 2-deoxy-β-glycoside formation.

7. Facile and robust methods for the regioselective acylation of N-acetylneuraminic acid.

8. Comparative Study on the Effects of Picoloyl Groups in Sialylations Based on Their Substitution Pattern.

9. 6-O-Picolinyl and 6-O-Picoloyl Building Blocks As Glycosyl Donors with Switchable Stereoselectivity.

10. Automated Glycan Assembly: A Perspective.

1. Broadening the Scope of the Reverse Orthogonal Strategy for Oligosaccharide Synthesis.