Straightforward and EfficientSynthesis of (4R,6S)-4-(tert-Butyldimethyl­siloxy)-6-(hydroxymethyl)tetrahydropyran-2-one

doi:10.1055/S-2008-1077957

Paper

Straightforward and EfficientSynthesis of (4R,6S)-4-(tert-Butyldimethylsiloxy)-6-(hydroxymethyl)tetrahydropyran-2-one

Published Jul 15, 2008 · Zdenko Časar

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Abstract

A novel synthetic approach to (4R,6S)-4-(tert-butyldimethylsiloxy)-6-(hydroxymethyl)tetrahydropyran-2-one, a key precursor of statin side chain, is described. A prime feature of the presented strategy is the transformation of (4R,6S)-4-(tert-butyldimethylsiloxy)-6-(iodomethyl)tetrahydropyran-2-one to an acetate ester derivative and subsequent cleavage of an acetate protection by applying homogeneous tin catalysis. lodolactone used in the study is accessible by a new route in five steps from (S)-ethyl 4-chloro-3-hydroxybutanoate. This method overcomes many of the drawbacks associated with previously reported approaches. It gives the title compound in 21% over seven steps, which is the highest attained overall yield yet. The disclosed approach was realized in convenient and economical manner suitable for industrial use.

Study Snapshot

This novel synthetic approach provides the highest yield of (4R,6S)-4-(tert-butyldimethylsiloxy)-6-(hydroxymethyl)tetrahydropyran-2-one (21%), a key precursor of statin side chains, in a convenient and economical manner suitable for industrial

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

Straightforward and EfficientSynthesis of (4R,6S)-4-(tert-Butyldimethylsiloxy)-6-(hydroxymethyl)tetrahydropyran-2-one

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References

Citations

Engineered, highly productive biosynthesis of artificial, lactonized statin side-chain building blocks: The hidden potential of Escherichia coli unleashed.

This study developed a highly productive, cost-effective, and industrially scalable process for producing 6-substituted lactones in Escherichia coli, using endogenous DERA and membrane-bound PQQ-dependent glucose dehydrogenase.

Fluorine in pharmaceutical industry: fluorine-containing drugs introduced to the market in the last decade (2001-2011).

Fluorine-containing drugs have been introduced to the pharmaceutical market in the last decade (2001-2011), with a focus on enhancing the effectiveness of existing drugs and developing new ones.

Conformational Analysis of Geometric Isomers of Pitavastatin Together with Their Lactonized Analogues

Z-isomeric pitavastatin analogues show more flexibility in attaining numerous conformations compared to rosuvastatin analogues, potentially improving future drug design.

A Highly Productive, Whole-Cell DERA Chemoenzymatic Process for Production of Key Lactonized Side-Chain Intermediates in Statin Synthesis

This study developed a highly productive, whole-cell DERA biotransformation process for producing chiral lactol intermediates, which are essential for the synthesis of optically pure super-statins like rosuvastatin and pitavastatin.

Application of Flow Photochemical Bromination in the Synthesis of a 5-Bromomethylpyrimidine Precursor of Rosuvastatin: Improvement of Productivity and Product Purity

Flow photochemical bromination significantly increases reaction productivity and reduces side products, resulting in shorter reaction times and improved product purity compared to batch-mode synthesis.

Recent Progress in the Synthesis of Super-Statins

Recent developments in super-statin synthesis focus on novel approaches to forming chiral statin lateral chains and assembling these key units into the final super-statin structure.

Kinetic modeling of a crude DERA lysate-catalyzed process in synthesis of statin intermediates

The study developed a three-step kinetic model for the DERA-catalyzed reaction, which can optimize reactor design and achieve higher concentrations of desired statin intermediates.

Straightforward and EfficientSynthesis of (4R,6S)-4-(tert-Butyldimethyl­siloxy)-6-(hydroxymethyl)tetrahydropyran-2-one

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References

Citations

Engineered, highly productive biosynthesis of artificial, lactonized statin side-chain building blocks: The hidden potential of Escherichia coli unleashed.

This study developed a highly productive, cost-effective, and industrially scalable process for producing 6-substituted lactones in Escherichia coli, using endogenous DERA and membrane-bound PQQ-dependent glucose dehydrogenase.

Fluorine in pharmaceutical industry: fluorine-containing drugs introduced to the market in the last decade (2001-2011).

Fluorine-containing drugs have been introduced to the pharmaceutical market in the last decade (2001-2011), with a focus on enhancing the effectiveness of existing drugs and developing new ones.

Conformational Analysis of Geometric Isomers of Pitavastatin Together with Their Lactonized Analogues

Z-isomeric pitavastatin analogues show more flexibility in attaining numerous conformations compared to rosuvastatin analogues, potentially improving future drug design.

A Highly Productive, Whole-Cell DERA Chemoenzymatic Process for Production of Key Lactonized Side-Chain Intermediates in Statin Synthesis

This study developed a highly productive, whole-cell DERA biotransformation process for producing chiral lactol intermediates, which are essential for the synthesis of optically pure super-statins like rosuvastatin and pitavastatin.

Application of Flow Photochemical Bromination in the Synthesis of a 5-Bromomethylpyrimidine Precursor of Rosuvastatin: Improvement of Productivity and Product Purity

Flow photochemical bromination significantly increases reaction productivity and reduces side products, resulting in shorter reaction times and improved product purity compared to batch-mode synthesis.

Recent Progress in the Synthesis of Super-Statins

Recent developments in super-statin synthesis focus on novel approaches to forming chiral statin lateral chains and assembling these key units into the final super-statin structure.

Kinetic modeling of a crude DERA lysate-catalyzed process in synthesis of statin intermediates

The study developed a three-step kinetic model for the DERA-catalyzed reaction, which can optimize reactor design and achieve higher concentrations of desired statin intermediates.

Straightforward and EfficientSynthesis of (4R,6S)-4-(tert-Butyldimethylsiloxy)-6-(hydroxymethyl)tetrahydropyran-2-one