156769-15-2

Basic information

• Product Name: meso-2,3-bis[(3,4-dimethoxyphenyl)methyl]-butane-1,4-diol
• Synonyms: meso-2,3-bis[(3,4-dimethoxyphenyl)methyl]-butane-1,4-diol
• CAS NO: 156769-15-2
• Molecular Weight: 390.477
• Mol File: 156769-15-2.mol

Chemical Properties

• CAS DataBase Reference: meso-2,3-bis[(3,4-dimethoxyphenyl)methyl]-butane-1,4-diol(CAS DataBase Reference)
• NIST Chemistry Reference: meso-2,3-bis[(3,4-dimethoxyphenyl)methyl]-butane-1,4-diol(156769-15-2)
• EPA Substance Registry System: meso-2,3-bis[(3,4-dimethoxyphenyl)methyl]-butane-1,4-diol(156769-15-2)

Safety Data

• Hazardous Substances Data: 156769-15-2(Hazardous Substances Data)

Upstream product

• 73119-35-4 2,3-bis(3,4-dimethoxybenzylidene)butanedioic acid 
• 42923-56-8 veratrylidene-succinic acid dimethyl ester 
• 5507-27-7 3,4-dimethoxybenzylidenesuccinic acid 
• 156769-14-1 (E) 3-(3,4-dimethoxy-benzylidene)-4-(3,4-dimethoxybenzyl)-4,5-dihydro-(3H)-furanone 
• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 72430-92-3 4-[(3,4-dimethoxyphenyl)methyl]dihydrofuran-2-one 
• 259540-45-9 (2R,3S)-1,4-bis((4R,5S)-3,4-dimethyl-2-oxo-5-phenylimidazolidinyl)-2,3-bis[(3,4-dimethoxyphenyl)methyl]butane-1,4-dione 
• 126965-32-0 meso-1,2-bis[(3,4-dimethoxyphenyl)methyl]ethane-1,2-dicarboxylic acid 
• 4773-01-7 (3S*,4R*)-3-(3,4-dimethoxybenzyl)-4-(3,4-dimethoxybenzyl)-4,5-dihydro-2(3H)-furanone 
• 163732-94-3 meso-2,3-diveratryl-succinic acid dimethyl ester 

Downstream Products

• 24150-24-1 terameprocol 
• 521-54-0 (±)-isogalbulin 
• 81446-31-3 (+)-O-Methyl-isoarctigenin 
• 215377-61-0 (2R,3S)-4-Acetoxy-2,3-bis-(3,4-dimethoxy-benzyl)-butyric acid 
• 215377-59-6 (2S,3R)-4-Acetoxy-2,3-bis-(3,4-dimethoxy-benzyl)-butyric acid 
• 215377-60-9 Acetic acid (2S,3R)-2-(3,4-dimethoxy-benzyl)-4-(3,4-dimethoxy-phenyl)-3-hydroxymethyl-butyl ester 
• 215377-58-5 Acetic acid (2R,3S)-3-acetoxymethyl-2-(3,4-dimethoxy-benzyl)-4-(3,4-dimethoxy-phenyl)-butyl ester 
• 215377-57-4 Acetic acid (2R,3S)-2-(3,4-dimethoxy-benzyl)-4-(3,4-dimethoxy-phenyl)-3-hydroxymethyl-butyl ester 
• 156769-16-3 (2R*,3S*)-2,3-(methanesulfonyloxymethyl)-1,4-bis-(3,4-dimethoxyphenyl)butane 
• 876026-47-0 cis-3,4-Diveratryl-tetrahydro-furan 

Relevant articles and documents

A sterically encumbered photoredox catalyst enables the unified synthesis of the classical lignan family of natural products

Herein, we detail a unified synthetic approach to the classical lignan family of natural products that hinges on divergence from a common intermediate that was strategically identified from nature's biosynthetic blueprints. Efforts toward accessing the common intermediate through a convergent and modular approach resulted in the discovery of a sterically encumbered photoredox catalyst that can selectively generate carbonyl ylides from electron-rich epoxides. These can undergo concerted [3 + 2] dipolar cycloadditions to afford tetrahydrofurans, which were advanced (2-4 steps) to at least one representative natural product or natural product scaffold within all six subtypes in classical lignans. The application of those synthetic blueprints to the synthesis of heterolignans bearing unnatural functionality was demonstrated, which establishes the potential of this strategy to accelerate structure-activity-relationship studies of these natural product frameworks and their rich biological activity.

Oxidative Homocoupling of Chiral 3-Arylpropanoic Acid Derivatives. Application to Asymmetric Synthesis of Lignans

The oxidative homocouplings of lithium enolates of (4S)-3-(3-arylpropanoyl)-4-isopropyl-2-oxazolidinones and (4R,5S)-1-(3-arylpropanoyl)-3,4-dimethyl-5-phenyl-2-imidazolidinones gave the corresponding R,R-dimers stereoselectively with TiCl4, Ph

A chemoenzymatic synthesis of both enantiomers of a cis-lignan lactone

The stereoselective acetylation of meso-2,3-bis(3,4- dimethoxybenzyl)butanediol by vinyl acetate in the presence of Candida antarctica lipase in benzene gave the corresponding (+)-(2S,3R) monoester (ee ≥98%). Transesterification of meso-2,3-bis(3,4-dimethoxybenzyl)butyl diacetate, in the presence of the same enzyme, by ethanol in benzene/isopropyl ether gave the corresponding (-)-(2R,3S) monoester (ee ≥98%). Both enantiomers of the known cis-2,3-bis(3,4- dimethoxybenzyl)butyrolactone were synthesized from these monoesters.

Ruthenium dioxide in fluoro acid medium V. Application to the non phenolic oxidative coupling of diarylbutanes. Conformational studies of cis and trans deoxyschizandrins

Ruthenium (IV) dioxide dihydrate in fluoro acidic medium was found to be a very efficient agent for the non phenolic oxidative coupling of diarylbutanes. We observed along with the expected aryl-aryl coupling, an unusual aryl-benzyl coupling, leading to a known class of lignans, the aryltetralins. Conformational studies of resultant cis and trans deoxyschizandrins were performed using high resolution NMR and molecular models.