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Related Concept Videos

Protecting Groups for Aldehydes and Ketones: Introduction01:23

Protecting Groups for Aldehydes and Ketones: Introduction

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Protecting groups are compounds that can bind to a specific functional group in the presence of other functional groups to protect them from undesired chemical reactions. These compounds can selectively bind to particular functional groups and advance chemoselective reactions in polyfunctional systems (Figure 1). After the functional group has served its purpose, it is removed by reacting it with specific compounds.
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Acetals and Thioacetals as Protecting Groups for Aldehydes and Ketones01:24

Acetals and Thioacetals as Protecting Groups for Aldehydes and Ketones

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Acetals are formed by reacting two equivalents of alcohol with carbonyl compounds like aldehydes or ketones. Acetals are unaffected by bases, nucleophiles, oxidizing agents, and reducing agents. They serve as protecting groups for aldehydes and ketones. Acetals can be easily formed and also easily removed via mild acid hydrolysis.
In the presence of multiple functional groups, when selective reduction of one group over the other is desired, groups like aldehydes and ketones that form acetals...
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Oligosaccharide Assembly01:24

Oligosaccharide Assembly

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Protein glycosylation starts in the ER lumen and continues in the Golgi apparatus. Glycosyltransferases catalyze the addition of sugar molecules or glycosylation of proteins. Usually, these enzymes add sugars to the hydroxyl groups of selected serine or threonine residues to form O-linked glycans or the amino groups of asparagine residues to form N-linked glycans. Different positions on the same polypeptide chain can contain differently linked glycans.
Multiple sugar molecules that may or may...
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Protection of Alcohols02:31

Protection of Alcohols

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This lesson delves into the concept of protection and deprotection of a functional group fundamental to synthetic organic chemistry. These phenomena are explained in the context of aliphatic and aromatic alcohols.
Protection
It defines a protecting group as the masking agent to make the more reactive species inert to a given set of conditions. This concept is depicted via the illustration of liquid flow through different outlets in an assembly of pipes. The analogy helps to understand the role...
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Alkylation of β-Diester Enolates: Malonic Ester Synthesis01:14

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Malonic ester synthesis is a method to obtain α substituted carboxylic acids from ꞵ-diesters such as diethyl malonate and alkyl halides.
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Alkylation of β-Ketoester Enolates: Acetoacetic Ester Synthesis01:07

Alkylation of β-Ketoester Enolates: Acetoacetic Ester Synthesis

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Acetoacetic ester synthesis is a method to obtain ketones from alkyl halides and β-keto esters. The reaction occurs in the presence of an alkoxide base that abstracts the acidic proton of the β-keto esters. The step results in an enolate ion which is doubly stabilized. The enolate then reacts with an alkyl halide via the SN2 process to produce an alkylated ester intermediate with a new C–C bond. The hydrolysis of the intermediate, followed by acidification, results in an...
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Related Experiment Video

Updated: May 3, 2026

Regioselective O-Glycosylation of Nucleosides via the Temporary 2',3'-Diol Protection by a Boronic Ester for the Synthesis of Disaccharide Nucleosides
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Regioselective O-Glycosylation of Nucleosides via the Temporary 2',3'-Diol Protection by a Boronic Ester for the Synthesis of Disaccharide Nucleosides

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Tunable acid-sensitive ester protecting groups in oligosaccharide synthesis.

Yao Li1, Xinyu Liu

  • 1Department of Chemistry, University of Pittsburgh, 219 Parkman Avenue, Pittsburgh, PA 15260, USA. xinyuliu@pitt.edu.

Chemical Communications (Cambridge, England)
|February 13, 2014
PubMed
Summary

New acid-cleavable ester protecting groups were developed for oligosaccharide synthesis. Trifluoroacetic acid (TFA) in toluene effectively removes these groups, simplifying the process.

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Area of Science:

  • Carbohydrate Chemistry
  • Organic Synthesis
  • Protecting Group Strategies

Background:

  • Oligosaccharide synthesis requires precise control over protecting groups.
  • Existing protecting groups like 2-naphthylmethyl (NAP) and p-methoxybenzyl (PMB) ethers have limitations in acid sensitivity.
  • Development of novel protecting groups is crucial for efficient synthesis.

Purpose of the Study:

  • To design and synthesize novel acid-cleavable ester-type protecting groups.
  • To evaluate the acid-sensitivity profiles of these new groups.
  • To identify an effective deprotection method for global removal in oligosaccharide synthesis.

Main Methods:

  • Synthesis of a series of ester-type protecting groups.
  • Assessment of acid-sensitivity profiles by comparison with known protecting groups (NAP, PMB).
  • Testing of trifluoroacetic acid (TFA) in toluene as a deblocking cocktail.

Main Results:

  • Successfully designed and synthesized novel acid-cleavable ester protecting groups.
  • These groups exhibit acid-sensitivity profiles comparable to NAP and PMB ethers.
  • Trifluoroacetic acid (TFA) in toluene proved to be a simple and effective deblocking cocktail for global removal.

Conclusions:

  • The newly developed ester protecting groups offer a viable alternative for oligosaccharide synthesis.
  • The TFA/toluene deblocking cocktail provides an efficient method for their removal.
  • These advancements facilitate more streamlined and effective oligosaccharide construction.