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Related Concept Videos

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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Preparation of 1° Amines: Gabriel Synthesis01:28

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Direct alkylation is not a suitable method for synthesizing amines because it produces polyalkylated products. Gabriel synthesis is the most preferred method to exclusively make primary amines. The method uses phthalimide, which contains a protected form of nitrogen that participates in alkylation only once to predominantly give primary amines.
Strong bases like NaOH or KOH deprotonate the phthalimide to form the corresponding anion, which acts as a nucleophile. Further, the anion attacks an...
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Preparation and Reactions of Sulfides02:26

Preparation and Reactions of Sulfides

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Sulfides are the sulfur analog of ethers, just as thiols are the sulfur analog of alcohol. Like ethers, sulfides also consist of two hydrocarbon groups bonded to the central sulfur atom. Depending upon the type of groups present, sulfides can be symmetrical or asymmetrical. Symmetrical sulfides can be prepared via an SN2 reaction between 2 equivalents of an alkyl halide and one equivalent of sodium sulfide.
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Preparation of Amides01:29

Preparation of Amides

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Amides are synthesized by treating carboxylic acids with amines in the presence of dehydrating agents like dicyclohexylcarbodiimide (DCC).
The DCC-promoted synthesis of amides begins with the protonation of DCC by carboxylic acid. The protonation makes it a better acceptor. Next, the addition of carboxylate to the protonated carbodiimide gives a reactive acylating agent.
Subsequently, the amine acts as a nucleophile that attacks the acylating agent to form a tetrahedral intermediate. In the...
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Preparation of Alkynes: Alkylation Reaction02:27

Preparation of Alkynes: Alkylation Reaction

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Introduction
Alkylation of terminal alkynes with primary alkyl halides in the presence of a strong base like sodium amide is one of the common methods for the synthesis of longer carbon-chain alkynes. For example, treatment of 1-propyne with sodium amide followed by reaction with ethyl bromide yields 2-pentyne.
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Preparation and Reactions of Thiols02:33

Preparation and Reactions of Thiols

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Thiols are prepared using the hydrosulfide anion as a nucleophile in a nucleophilic substitution reaction with alkyl halides. For instance, bromobutane reacts with sodium hydrosulfide to give butanethiol.
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Related Experiment Video

Updated: May 5, 2026

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Glycosyl Thioimidates as Versatile Building Blocks for Organic Synthesis.

S J Hasty1, A V Demchenko

  • 1University of Missouri - St. Louis, One University Boulevard, St. Louis, Missouri 63121, USA.

Chemistry of Heterocyclic Compounds
|November 30, 2013
PubMed
Summary

This review covers glycosyl thioimidates, focusing on heterocyclic derivatives like S-benzothiazolyl (SBaz) and S-benzoxazolyl (SBox) glycosides. These compounds enable highly diastereoselective glycosylation for efficient oligosaccharide synthesis.

Keywords:
carbohydratesglycoconjugatesglycosylationleaving groupoligosaccharidesthioimidates

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Area of Science:

  • Carbohydrate Chemistry
  • Organic Synthesis
  • Glycobiology

Background:

  • Glycosylation is crucial for synthesizing complex carbohydrates like oligosaccharides.
  • Developing efficient and stereoselective glycosylation methods remains a challenge in carbohydrate chemistry.

Purpose of the Study:

  • To review the synthesis and applications of glycosyl thioimidates in chemical glycosylation.
  • To highlight the utility of specific heterocyclic glycosyl thioimidates as anomeric leaving groups.

Main Methods:

  • Discussion of synthetic routes for various glycosyl thioimidates.
  • Analysis of the application of these thioimidates in glycosylation reactions.
  • Focus on S-benzothiazolyl (SBaz), S-benzoxazolyl (SBox), S-thiazolinyl (STaz), and S-benzimidazolyl (SBiz) glycosides.

Main Results:

  • Heterocyclic moieties like SBaz, SBox, STaz, and SBiz function as excellent anomeric leaving groups.
  • These leaving groups facilitate highly diastereoselective glycosylation reactions.
  • The use of these thioimidates provides streamlined access to oligosaccharides.

Conclusions:

  • Glycosyl thioimidates, particularly heterocyclic variants, are powerful tools for stereoselective glycosylation.
  • These compounds significantly advance the field of oligosaccharide assembly.
  • The reviewed thioimidates offer a promising strategy for efficient carbohydrate synthesis.