Facile synthesis of enantiomerically pure 1-(5-bromo-2-chlorophenyl)-1-(4-ethoxyphenyl)ethane

doi:10.1007/s40242-014-3257-1

Paper

Facile synthesis of enantiomerically pure 1-(5-bromo-2-chlorophenyl)-1-(4-ethoxyphenyl)ethane

Published Mar 11, 2014 · Shuo Zhang, Wenjin Wang, Chuan Li

Chemical Research in Chinese Universities

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Abstract

A facile 7-step procedure for the synthesis of enantiomerically pure 1-(5-bromo-2-chlorophenyl)-1-(4-ethoxyphenyl)ethanes[(R)-2 and(S)-2] that started from (5-bromo-2-chlorophenyl)(4-ethoxyphenyl)methanone 3 was developed. The key step was the resolution of 2-(5-bromo-2-chlorophenyl)-2-(4-ethoxyphenyl)acetic acid 6 by crystallizations of its L- and D-menthyl esters 7 and 8 from petroleum ether to give optically pure enantiomers 9 and 10, respectively. The absolute configurations of the products were unambiguously determined by single-crystal X-ray diffractions of four key intermediates, 9, 10, 13 and 14. This procedure is characterized by inexpensiveness, scalability and ability to produce two individual enantiomers of a diarylethane with unambiguously determined absolute configurations and high enantiomeric purities.

Study Snapshot

This facile 7-step procedure efficiently synthesizes enantiomerically pure 1-(5-bromo-2-chlorophenyl)-1-(4-ethoxyphenyl)ethanes with high enantiomeric purity and unambiguous absolute configurations.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

Facile synthesis of enantiomerically pure 1-(5-bromo-2-chlorophenyl)-1-(4-ethoxyphenyl)ethane

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References

Design, synthesis and biological activity of cyclohexane-bearing C-glucoside derivatives as SGLT2 inhibitors

Cyclohexane-bearing C-glucoside derivatives, particularly the 6-deoxy derivative of 1, show potential as potent SGLT2 inhibitors, causing more urinary glucose excretion than 1, dapagliflozin, and other drugs.

Total Synthesis of α-Elvucitabine

-Elvucitabine was successfully synthesized in 26% overall yield using a nine-step procedure starting from L-lyxose, with TMSOTf-mediated stereocontrolled -N-glycosidation and olefination being key steps.

Design and synthesis of C2-symmetric N-heterocyclic carbene precursors and metal carbenoids.

Chiral C2-symmetric imidazolium and imidazolinium ions and their metal-bound carbenoids show potential for enantioselective hydrosilylation of acetophenone.

Discovery of a clinical candidate from the structurally unique dioxa-bicyclo[3.2.1]octane class of sodium-dependent glucose cotransporter 2 inhibitors.

Compound 4 (PF-04971729) is a promising type 2 diabetes treatment with a unique structural design and excellent preclinical safety profile.

Stereospecific nickel-catalyzed cross-coupling reactions of alkyl ethers: enantioselective synthesis of diarylethanes.

Nickel-catalyzed cross-coupling reactions of alkyl ethers enable facile enantioselective synthesis of biologically active diarylethanes from readily available optically enriched carbinols.

Palladium-catalyzed cross-coupling reaction of secondary benzylic bromides with grignard reagents.

The palladium-catalyzed Kumada-Corriu reaction allows for the cross-coupling of secondary benzylic bromides with aryl and alkenyl Grignard reagents, yielding acceptable to good yields and minimizing undesired beta-el

Novel L-xylose derivatives as selective sodium-dependent glucose cotransporter 2 (SGLT2) inhibitors for the treatment of type 2 diabetes.

O-xyloside 7c shows potential as a selective SGLT2 inhibitor for treating type 2 diabetes by maintaining glucose homeostasis in diabetic patients.

Cross coupling reactions of chiral secondary organoboronic esters with retention of configuration.

Chiral secondary boronic esters can be cross-coupled with high yields and retention of configuration, with the exception of linear boronate ester, under specific conditions.

Development of the renal glucose reabsorption inhibitors: a new mechanism for the pharmacotherapy of diabetes mellitus type 2.

Renal glucose reabsorption inhibitors show potential as a new treatment for diabetes mellitus type 2, offering a new approach to achieving HbA1C target levels and potentially reducing the need for insulin therapy.

Citations

Characterising Supramolecular Architectures in Crystals Featuring I⋯Br Halogen Bonding: Persistence of X⋯X’ Secondary-Bonding in Their Congeners

Crystals with I-Br secondary-bonding show diverse supramolecular architectures and potential for crystal engineering, offering surprises and opportunities.