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Updated: Jun 22, 2026

Regioselective O-Glycosylation of Nucleosides via the Temporary 2',3'-Diol Protection by a Boronic Ester for the Synthesis of Disaccharide Nucleosides
08:46

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

Published on: July 26, 2018

アルファ-2-デオキシ-2-アミノグリコシドのニッケル触媒によるステレオ選択的形成

Enoch A Mensah1, Hien M Nguyen

  • 1Department of Chemistry and Biochemistry, Montana State University, Bozeman, Montana 59717, USA.

Journal of the American Chemical Society
|June 6, 2009
PubMed
まとめ

新しいニッケル触媒法により,アルファ-2-デオキシ-2-アミノグリコシドのステレオ選択的合成が可能になりました. この効率的なグリコシル化反応は,穏やかな条件下で進行し,高アルファ選択性を持つ貴重なグリココンジュガートを産生します.

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関連する概念動画

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Base-Catalyzed Aldol Addition Reaction

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Aldol Condensation with β-Diesters: Knoevenagel Condensation

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Alkylation of β-Diester Enolates: Malonic Ester Synthesis

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Aldehydes and Ketones with HCN: Cyanohydrin Formation Mechanism

Cyanohydrins are formed when cyanide nucleophiles and carbonyl compounds like aldehydes and ketones react. A strong base, the cyanide ion, catalyzes cyanohydrin formation. The ions are generated from HCN under aqueous conditions. Once the cyanide ions are generated, the first step involves the nucleophilic attack of the cyanide ions on the electrophilic carbonyl carbon. This attack shifts the π electrons from the C=O to the oxygen atom forming the alkoxide ion intermediate. The alkoxide anion...
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Aldehydes and Ketones with HCN: Cyanohydrin Formation Overview

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 mixture.
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SN2 Reaction: Stereochemistry

In an SN2 reaction, the nucleophilic attack on the substrate and departure of the leaving group occurs simultaneously through a transition state. As the nucleophile approaches the substrate from the back-side, the configuration of the substrate carbon changes from tetrahedral to trigonal bipyramidal and then back to tetrahedral, leading to an inversion in the configuration of the product.
If the substrate is an achiral molecule at the α-carbon, the inversion of configuration is not observed.