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Related Concept Videos

Preparation of 1° Amines: Azide Synthesis01:22

Preparation of 1° Amines: Azide Synthesis

Direct alkylation of ammonia produces polyalkylated amines, along with a quaternary ammonium salt. To exclusively prepare primary amines, the azide synthesis method can be used.
Azide ions act as good nucleophiles and react with unhindered alkyl halides to form alkyl azides. Alkyl azides do not participate in further nucleophilic substitution reactions, thereby eliminating the chances of polyalkylated products. Alkyl azides are reduced by hydride-based reducing agents, like lithium aluminum...
Protection of Alcohols02:31

Protection of Alcohols

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...
Aldehydes and Ketones with Amines: Imine Formation Mechanism01:23

Aldehydes and Ketones with Amines: Imine Formation Mechanism

Imine formation involves the addition of carbonyl compounds to a primary amine. It begins with the generation of carbinolamine through a series of steps involving an initial nucleophilic attack and then several proton transfer reactions. The second part includes the elimination of water, as a leaving group, to give the imine.
Imines are formed under mildly acidic conditions. A pH of 4.5 is ideal for the reaction.
If the pH is low or the solution is too acidic, the reaction slows down in the...
Protecting Groups for Aldehydes and Ketones: Introduction01:23

Protecting Groups for Aldehydes and Ketones: Introduction

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.
Amines to Amides: Acylation of Amines01:19

Amines to Amides: Acylation of Amines

Various carboxylic acid derivatives (such as acid chlorides, esters, and anhydrides) can be used for the acylation of amines to yield amides. The reaction requires two equivalents of amines. The first amine molecule functions as a nucleophile and attacks the carbonyl carbon to produce a tetrahedral intermediate. This is followed by the loss of the leaving group and restoration of the C=O bond.
Next, the second equivalent of amine serves as a Brønsted base and deprotonates the quaternary amide...
Acetals and Thioacetals as Protecting Groups for Aldehydes and Ketones01:24

Acetals and Thioacetals as Protecting Groups for Aldehydes and Ketones

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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Preparation of Enantiopure Non-Activated Aziridines and Synthesis of Biemamide B, D, and epiallo-Isomuscarine
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A highly efficient azide-based protecting group for amines and alcohols.

Srinivasu Pothukanuri1, Nicolas Winssinger

  • 1Institut de Science et Ingénierie Supramoléculaires, Université Louis Pasteur - CNRS, 8 allée Gaspard Monge, 67000 Strasbourg, France.

Organic Letters
|May 8, 2007
PubMed
Summary

A novel azide-based carbamate/carbonate protecting group (Azoc) offers rapid, neutral deprotection. This Azoc group is orthogonal to Fmoc and Mtt, proving useful in peptide synthesis and beta-glycoside formation.

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Preparation of Enantiopure Non-Activated Aziridines and Synthesis of Biemamide B, D, and epiallo-Isomuscarine
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A Direct, Early Stage Guanidinylation Protocol for the Synthesis of Complex Aminoguanidine-containing Natural Products
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A Direct, Early Stage Guanidinylation Protocol for the Synthesis of Complex Aminoguanidine-containing Natural Products

Published on: September 9, 2016

Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry
  • Carbohydrate Chemistry

Background:

  • Protecting groups are essential in complex organic synthesis.
  • Orthogonality of protecting groups is crucial for selective deprotection strategies.
  • Efficient and mild deprotection methods are highly sought after in synthetic chemistry.

Purpose of the Study:

  • To introduce and characterize a new azide-based protecting group, Azoc.
  • To demonstrate the utility of Azoc in peptide synthesis.
  • To explore the application of Azoc in the formation of beta-glycosides.

Main Methods:

  • Synthesis of the azide-based carbamate/carbonate (Azoc) protecting group.
  • Deprotection studies using various phosphine reagents (trimethyl phosphine, tributyl phosphine, polymer-bound triphenyl phosphine) under neutral conditions.
  • Orthogonality testing with standard peptide synthesis protecting groups (Fmoc, Mtt).
  • Application in beta-glycoside synthesis utilizing a 2-aminoglucosyl donor.

Main Results:

  • Azoc protecting groups can be efficiently removed in under 2 minutes under neutral conditions.
  • The Azoc group demonstrates orthogonality with Fmoc and Mtt protecting groups.
  • Successful synthesis of beta-glycosides was achieved, highlighting the utility of neighboring group participation.

Conclusions:

  • The Azoc protecting group offers a rapid and mild deprotection strategy.
  • Azoc is a valuable tool for orthogonal protection in peptide synthesis.
  • The Azoc group facilitates the synthesis of complex carbohydrate structures like beta-glycosides.