Dimethyl 3,4,5,6‐[2H4] ‐2‐oxoheptylphosphonate: A readily available reagent for the preparation of deuterated prostanoids‐application to the synthesis of 2H4‐labelled (±)‐prostaglandin D2

doi:10.1002/JLCR.2580270310

Paper

Dimethyl 3,4,5,6‐[2H4] ‐2‐oxoheptylphosphonate: A readily available reagent for the preparation of deuterated prostanoids‐application to the synthesis of 2H4‐labelled (±)‐prostaglandin D2

Published Mar 1, 1989 · C. Meese, Sabine Holzer

Journal of Labelled Compounds and Radiopharmaceuticals

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Abstract

Dimethyl 3,4,5,6-[2H4]-2-oxoheptylphosphonate (1a) was conveniently prepared in two steps from ethyl sorbate and used in a total synthesis of low-blank (⩽ 0.2% 2Ho) 16,17,18,19-[2H4]-prostaglandin D2 (2a). The required allylic alcohol 15S-8 was isolated by fractional crystallisation of the mixture of R/S epimers and then transformed to a key intermediate, 15S-silyloxy compound 10, by regiocontrolled monosilylation of diol 9.

Study Snapshot

Dimethyl 3,4,5,6-[2H4]-2-oxoheptylphosphonate (1a) is a readily available reagent for the preparation of deuterated prostanoids, with potential applications in the synthesis of low-blank ( 0.2% 2H4]-pros

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

Dimethyl 3,4,5,6‐[2H4] ‐2‐oxoheptylphosphonate: A readily available reagent for the preparation of deuterated prostanoids‐application to the synthesis of 2H4‐labelled (±)‐prostaglandin D2

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References

Synthesis of deuterated eicosanoids

Deuterated eicosanoids are essential tools for organic trace analysis, biomedical studies, and mechanistic investigations on endogenous eicosanoids.

Dimethyl 3,3,4,4,.5,.5,6,6‐(2H8)‐6‐methoxycarbonyl‐2‐oxo‐hexanephosphonate, a versatile reagent for the synthesis of deuterated ω‐carboxy prostanoids

Dimethyl 3,3,4,4,.5,6,6(2H8)6methoxycarbonyl2oxohexanephosphonate (1a) is a versatile starting compound for the synthesis of various -carboxy prostanoic acid metabolites.

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This method provides a sensitive and specific method for quantifying thromboxane B2 in human urine, with normal urinary excretion rates ranging from 37-112 ng/24 h.

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The study presents a stable isotope dilution assay for simultaneous determination of 6-oxo-prostaglandin F1 alpha and 2,3-dinor-6-oxo-prostaglandin F1 alpha in human seminal fluid and urine, with low concentrations in semi

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The developed assay accurately quantifies prostaglandin D2 in plasma, with major circulating metabolites identified during intravenous infusion.

Mikropräparation ringdeuterierter prostaglandine

Ring-labelled prostaglandins can be used as internal standards for GC/MS analysis of biological samples and as substrates for the preparation of other labelled prostaglandin metabolites.

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Prostaglandin D analogues with 9 beta- and 9-deoxy configurations show the most potent inhibition of platelet aggregation, while metabolically stabilized analogues with bulky substituents show reduced antiaggregatory activity.

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This study presents a novel method for synthesising a versatile prostaglandin intermediate using homogenous catalytic deuteration of acetylene, offering potential for efficient preparation of prostaglandins.

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