Protection of phosphonate function by means of ethoxycarbonyl group. A new method for generation of reactive silyl phosphite intermediates.

doi:10.1246/BCSJ.55.239

Paper

Protection of phosphonate function by means of ethoxycarbonyl group. A new method for generation of reactive silyl phosphite intermediates.

Published 1982 · M. Sekine, H. Mori, T. Hata

Bulletin of the Chemical Society of Japan

Q2 SJR score

14

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0

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Abstract

Nucleoside ethoxycarbonylphosphonates were prepared by condensation of appropriately protected nucleosides with ethoxycarbonylphosphonic acid. They were easily converted by treatment with 1 M NaOH followed by trimethylsilylation to highly reactive bis(trimethylsilyl) nucleoside phosphite intermediates which were allowed in situ to react with water, diphenyl disulfide, 2,2′-dipyridyl disulfide, and aldehydes to afford the corresponding nucleoside phosphonates, nucleoside S-phenyl phosphorothioates, nucleoside phosphates, and nucleoside α-hydroxy phosphonates in good yields, respectively. The nucleoside phosphonates were further converted to nucleosides under mild acidic conditions. Thus, the ethoxycarbonyl group proved to serve as a versatile protecting group for not only H–P(O) but also HO–P(O) and hydroxyl groups of sugars.

Study Snapshot

The ethoxycarbonyl group serves as a versatile protecting group for phosphonate functions, enabling the generation of reactive silyl phosphite intermediates for various reactions.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

Protection of phosphonate function by means of ethoxycarbonyl group. A new method for generation of reactive silyl phosphite intermediates.

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References

Silyl Phosphites. XVIII. Versatile Utility of α-(Trimethylsilyloxy)alkylphosphonates as Key Intermediates for Transformation of Aldehydes into Several Carbonyl Derivatives

-(Trimethylsilyloxy)alkylphosphonates are versatile intermediates for transforming aldehydes into various carbonyl derivatives, including -substituted carboxylic esters and -substituted lactones.

Studies of Phosphorylation. IV. The Phosphorylation of Nucleosides with Phosphorus Trihalide

Phosphorylation of nucleosides with phosphorus trichloride can produce nucleoside 5′-phosphite, a key intermediate in nucleotide synthesis.

A New Method for the Phosphorylation of Alcohols by Means of Bromine and Dibenzylhydrogen Phosphite

This study presents a new method for phosphorylating alcohols with bromine and dibenzylhydrogen phosphite, leading to various alkyldihydrogen phosphates in good yields.

Separation of the Phosphoric Esters on the Filter Paper Chromatogram

Filter paper chromatography is a promising method for identifying and determining individual phosphoric esters in complex mixtures, offering diagnostic results for complex biological reactions.

Citations

Preparation of internucleotide phosphate analogues via the corresponding H‐phosphonate diester

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Acylphosphonates and their Derivatives

Acylphosphonates and their derivatives have diverse structures and biological aspects, with potential applications in various fields.

Synthesis, hydrolytic behavior, and anti-HIV activity of selected acyloxyalkyl esters of trisodium phosphonoformate (foscarnet sodium).

The dichlorophenyl analog 9a of trisodium phosphonoformate (foscarnet sodium) shows dose-dependent inhibition of HIV activity in H9 cells, with bioreversibility being investigated.

5'-Phosphonates of ribonucleosides and 2'-deoxyribonucleosides : synthesis and antiviral activity

5′-Phosphonates of ribonucleosides and 2′-deoxyribonucleosides show promising antiviral activity against various viruses, suggesting potential as a new antiviral agent.

METAL AND ORGANOMETALLOIDAL PHOSPHITES AND PHOSPHONATES

Dialkyl phosphonates offer versatile chemical reagents with potential for diverse reactions with metal and organometal halides, offering potential for new chemical applications.

Phosphorus Addition at sp2 Carbon

Phosphorus addition at sp2 carbon can be used for chemical synthesis, biological regulation, and industrial applications, with potential applications in chemical synthesis, biological regulation, and industrial uses.

Synthesis of Carbon-Phosphorus Bonds

This paper discusses recent advances in the synthesis of carbon-phosphorus bonds, focusing on various methods and their applications in creating organophosphorus compounds.