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Related Concept Videos

Preparation of Diols and Pinacol Rearrangement01:57

Preparation of Diols and Pinacol Rearrangement

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Compounds bearing two hydroxyl groups are known as diols. When the hydroxyl groups are located on adjacent carbon atoms, the diols are called vicinal diols or glycols. Under acidic conditions, vicinal diols undergo a specific reaction called pinacol rearrangement.
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Aldol Condensation with β-Diesters: Knoevenagel Condensation01:27

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The Knoevenagel condensation is an aldol-type reaction involving the condensation of aldehydes or ketones with active methylene compounds such as β-diesters to produce substituted olefins.
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Wolff–Kishner reduction involves converting aldehydes and ketones to alkanes using hydrazine and a base. The reaction converts a carbonyl group to a methylene group. The method was independently discovered by N. Kishner in 1911 and L. Wolff in 1912. The reduction is carried out in high-boiling solvents such as ethylene glycol and diethylene glycol because heat is required to deprotonate the N–H proton in one of the reaction steps.                                       ...
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Aldehydes and Ketones with HCN: Cyanohydrin Formation Overview01:32

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Cyanohydrins are compounds that contain –CN and –OH groups on the same carbon atom. They are formed by the nucleophilic addition of the cyanide ions to the carbonyl group. Cyanide ions are highly basic and nucleophilic and can be generated from HCN under aqueous conditions. However, since HCN is a weak acid, the number of cyanide ions generated is very small. Hence, a small amount of base or KCN/NaCN is added to HCN to increase the concentration of the cyanide ions in the reaction...
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Chemistry of Carbohydrates03:25

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Carbohydrates are an essential part of the diet in humans and animals. Grains, fruits, and vegetables are natural sources of carbohydrates that provide energy to the body, particularly through glucose, a simple sugar that is a component of starch and an ingredient in many staple foods. The stoichiometric formula (CH2O)n, where n is the number of carbons in the molecule represents carbohydrates. In other words, the ratio of carbon to hydrogen to oxygen is 1:2:1 in carbohydrate molecules. This...
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Updated: Mar 19, 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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Progress in Kdo-glycoside chemistry.

Paul Kosma1

  • 1University of Natural Resources and Life Sciences-Vienna, Department of Chemistry, Muthgasse 18, A-1190 Vienna, Austria.

Tetrahedron Letters
|June 9, 2016
PubMed
Summary
This summary is machine-generated.

Recent advances in glycosylation chemistry have improved yields and selectivity for 3-deoxy-D-manno-oct-2-ulosonic acid derivatives. New methods focus on protecting groups and anomeric activation to prevent side reactions.

Keywords:
GlycalGlycosyl donorKdoOligosaccharideSynthesis

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Area of Science:

  • Carbohydrate Chemistry
  • Organic Synthesis
  • Glycoscience

Background:

  • 3-deoxy-D-manno-oct-2-ulosonic acid (Kdo) is a key component of bacterial lipopolysaccharides.
  • Efficient synthesis of Kdo glycosides is crucial for glycobiology and drug development.
  • Previous synthetic routes often suffered from low yields and poor stereocontrol.

Purpose of the Study:

  • To review recent developments in the glycosylation chemistry of Kdo units.
  • To highlight strategies for improving yields and anomeric selectivity.
  • To discuss methods for suppressing elimination side reactions during Kdo glycosylation.

Main Methods:

  • Review of literature on Kdo glycosylation strategies.
  • Analysis of protecting group effects on reactivity and selectivity.
  • Evaluation of different activation methods for the anomeric center.

Main Results:

  • Significant improvements in glycosylation yields and anomeric selectivity have been achieved.
  • The judicious selection of protecting groups effectively suppresses elimination side reactions.
  • Optimized activation protocols enhance the efficiency of Kdo glycosylation.

Conclusions:

  • Modern glycosylation techniques offer enhanced control over Kdo unit synthesis.
  • These advancements facilitate the preparation of complex glycoconjugates containing Kdo.
  • The reviewed strategies provide a valuable resource for researchers in carbohydrate chemistry.