4375-03-5

Basic information

• Product Name: [1R,(-)]-1α,4β-Bis(3,4-dimethoxyphenyl)-3aα,4,6,6aα-tetrahydro-1H,3H-furo[3,4-c]furan
• Synonyms: [1R,(-)]-1α,4β-Bis(3,4-dimethoxyphenyl)-3aα,4,6,6aα-tetrahydro-1H,3H-furo[3,4-c]furan;Epieudesamin;Epieudesmin;Symplocosigenol dimethyl ether
• CAS NO: 4375-03-5
• Molecular Formula: C₂₂H₂₆O₆
• Molecular Weight: 386.43824
• Mol File: 4375-03-5.mol
• Article Data: 11

Chemical Properties

• Appearance: /
• CAS DataBase Reference: [1R,(-)]-1α,4β-Bis(3,4-dimethoxyphenyl)-3aα,4,6,6aα-tetrahydro-1H,3H-furo[3,4-c]furan(CAS DataBase Reference)
• NIST Chemistry Reference: [1R,(-)]-1α,4β-Bis(3,4-dimethoxyphenyl)-3aα,4,6,6aα-tetrahydro-1H,3H-furo[3,4-c]furan(4375-03-5)
• EPA Substance Registry System: [1R,(-)]-1α,4β-Bis(3,4-dimethoxyphenyl)-3aα,4,6,6aα-tetrahydro-1H,3H-furo[3,4-c]furan(4375-03-5)

Safety Data

• Hazardous Substances Data: 4375-03-5(Hazardous Substances Data)

Upstream product

• 186581-53-3 diazomethane 
• 10061-38-8 (-)-epipinoresinol 
• 77-78-1 dimethyl sulfate 
• 487-36-5 (+/-)-pinoresinol 
• 63281-70-9 2,6-bis-(4-acetoxy-3-methoxyphenyl)-3,7-dioxabicyclo<3.3.0>octane-4,8-dione 
• 72536-38-0 4,8-dimethoxyeudesmin 
• 72536-37-9 4,8-dimethoxypinoresinol 
• 72536-34-6 4,8-dihydroxyeudesmin 
• 72536-33-5 4,8-dihydroxypinoresinol 
• 38209-42-6 threo-2,3-bis-(α-hydroxy-4-hydroxy-3-methoxybenzyl)butane-1,4-diol 
• 69854-19-9 2,6-bis-(3,4-dimethoxyphenyl)-3,7-dioxabicyclo<3.3.0>octane-4,8-dione 
• 77550-11-9 4-cis,8-cis-bis(4-hydroxy-3-methoxyphenyl)-3,7-dioxabicyclo<3.3.0>octane-2,6-dione 
• 1135-24-6 (E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid 
• 203924-93-0 1-(3,4-dimethoxyphenyl)-2,3-epoxypropan-1-ol 

Downstream Products

• 58311-18-5 (2R,3R)-2,3-bis[(3,4-dimethoxyphenyl)methyl]butane-1,4-diol 
• 60102-89-8 (+)-epipinoresinol dimethyl ether 
• 20610-45-1 (3aR)-1c,4c-bis-(2-bromo-4,5-dimethoxy-phenyl)-(3ar,6ac)-tetrahydro-furo[3,4-c]furan 
• 20610-45-1 (+/-)-1c,4c-bis-(2-bromo-4,5-dimethoxy-phenyl)-(3ar,6ac)-tetrahydro-furo[3,4-c]furan 
• 67560-68-3 tetrahydro-2-(3,4-dimethoxyphenyl)-4-<(3,4-dimethoxyphenyl)methyl>-3-furanmethanol 
• 4263-88-1 pinoresinol 
• 487-39-8 (+)-pinoresinol monomethyl ether 
• 20610-45-1 (3aS)-1c,4t-bis-(2-bromo-4,5-dimethoxy-phenyl)-(3ar,6ac)-tetrahydro-furo[3,4-c]furan 
• 20610-45-1 (3aS)-1c,4c-bis-(2-bromo-4,5-dimethoxy-phenyl)-(3ar,6ac)-tetrahydro-furo[3,4-c]furan 
• 81446-29-9 (-)-pinoresinol 
• 80900-41-0 2,5-bis(3,4-dimethoxyphenyl)-4-pyrone-3-carbinol 
• 20610-45-1 (3aR)-1c,4t-bis-(2-bromo-4,5-dimethoxy-phenyl)-(3ar,6ac)-tetrahydro-furo[3,4-c]furan 

Relevant articles and documents

Stereoselective total synthesis of furofuran lignans through dianion aldol condensation

Highly stereoselective total synthesis of (+)-eudesmin, (+)-yangambin, (-)-eudesmin, and (-)-yangambin is described. This method is useful to generate the core skeleton of furofuran rings utilizing modification of Evans asymmetric aldol condensation.

Stereoselective intramolecular coupling of diaroylacetates of (1R,1′R)-exo,exo′-3,3′-biisoborneol by oxidation with Br 2

The oxidative coupling of diaroylacetate derivatives prepared from (1R,1′R)-exo,exo′-3,3′-biisoborneol with NaH-Br2 gave the corresponding intramolecularly coupled products stereoselectively. The major (R,R)-isomers thus obtained were transformed to (-)-Sesamin and (-)-Eudesmin.

Stereoselective homocoupling of chiral 1-aroylacetyl-2-imidazolidinones by oxidation with Br2

The oxidative coupling of sodium enolates of (4R,5S)-1-aroylacetyl-3,4-dimethyl-5-phenyl-2-imidazolidinones with Br2 as the oxidant affords the R,R-dimers stereoselectively. The R,R-selectivity can be explained by a radical coupling mechanism.