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

• 7647-01-0 hydrogenchloride 
• 60102-89-8 (+)-epipinoresinol dimethyl ether 
• 133-03-9 (-)-asarinin 
• 620945-82-6 3-(3,4-Dimethoxy-phenyl)-3-oxo-propionic acid (1R,2S,3R,4R,1'R,2'S,3'R,4'R)-3'-[3-(3,4-dimethoxy-phenyl)-3-oxo-propionyloxy]-4,7,7,4',7',7'-hexamethyl-[2,2']bi[bicyclo[2.2.1]heptyl]-3-yl ester 
• 620945-81-5 3-(3,4-Dimethoxy-phenyl)-3-hydroxy-propionic acid (1R,2S,3R,4R,1'R,2'S,3'R,4'R)-3'-[3-(3,4-dimethoxy-phenyl)-3-hydroxy-propionyloxy]-4,7,7,4',7',7'-hexamethyl-[2,2']bi[bicyclo[2.2.1]heptyl]-3-yl ester 
• 77-78-1 dimethyl sulfate 
• 203924-93-0 1-(3,4-dimethoxyphenyl)-2,3-epoxypropan-1-ol 
• 72536-33-5 4,8-dihydroxypinoresinol 
• 32971-25-8 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 
• 38209-42-6 threo-2,3-bis-(α-hydroxy-4-hydroxy-3-methoxybenzyl)butane-1,4-diol 

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 
• 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 
• 3395-03-7 4,5-dimethoxy-1,2-dinitrobenzene 
• 93-07-2 Veratric acid 
• 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.

Sesquineolignans and other constituents from the seeds of Joannesia princeps

From the as extract of the seeds of the Brazilian Joannesia princeps 3,3′-bisdemethylpinoresinol and six new sesquineolignans were isolated besides the known neolignans americanol A, isoamericanol A and isoamericanin A which were found to be the major constituents. A method was developed to distinguish americanol- from isoamericanol-type compounds spectroscopically.

Short and stereoselective total synthesis of furano lignans (±)-dihydrosesamin, (±)-lariciresinol dimethyl ether, (±)-acuminatin methyl ether, (±)-sanshodiol methyl ether, (±)-lariciresinol, (±)-acuminatin, and (±)-lariciresinol

Intramolecular radical cyclization of suitably substituted epoxy ethers 4a-g using bis(cyclopentadienyl)titanium(III) chloride as the radical source resulted in trisubstituted tetrahydrofurano lignans and 2,6-diaryl-3,7-dioxabicyclo [3.3.0] octane lignans depending on the reaction conditions. The titanium(III) species was prepared in situ from commercially available titanocene dichloride and activated zinc dust in THF. Upon radical cyclization followed by acidic workup, epoxy olefinic ethers 4a-g afforded furano lignans dihydrosesamin 1a, lariciresinol dimethyl ether lb, acuminatin methyl ether le, and sanshodiol methyl ether 1g directly and lariciresinol 1h, acuminatin li, and lariciresinol monomethyl ether 1j after removal of the benzyl protecting group by controlled hydrogenolysis of the corresponding cyclized products. The furofuran lignans sesamin 2a, eudesmin 2b, and piperitol methyl ether 2e were also prepared directly by using the same precursors 4a-f on radical cyclization followed by treatment with iodine and pinoresinol 2h, piperitol 2i, and pinoresinol monomethyl ether 2j after controlled hydrogenolysis of the benzyl protecting group of the corresponding cyclized products. Two naturally occurring acyclic lignans, secoisolariciresinol 5h and secoisolariciresinol dimethyl ether 5b, have also been prepared by exhaustive hydrogenolysis of 2h and 2b, respectively.