60102-89-8

Basic information

• Product Name: (+)-epipinoresinol dimethyl ether
• Synonyms: (+)-epipinoresinol dimethyl ether
• CAS NO: 60102-89-8
• Molecular Weight: 386.445
• Mol File: 60102-89-8.mol
• Article Data: 14

Chemical Properties

• CAS DataBase Reference: (+)-epipinoresinol dimethyl ether(CAS DataBase Reference)
• NIST Chemistry Reference: (+)-epipinoresinol dimethyl ether(60102-89-8)
• EPA Substance Registry System: (+)-epipinoresinol dimethyl ether(60102-89-8)

Safety Data

• Hazardous Substances Data: 60102-89-8(Hazardous Substances Data)

Upstream product

• 526-06-7 eudesmin 
• 7647-01-0 hydrogenchloride 
• 64-17-5 ethanol 
• 7664-93-9 sulfuric acid 
• 64-19-7 acetic acid 
• 77-78-1 dimethyl sulfate 
• 4263-88-1 pinoresinol 
• 487-36-5 (+)-epipinoresinol 
• 74-88-4 methyl iodide 
• 52200-05-2 4-methanesulfonyloxy-3-methoxybenzaldehyde 
• 651779-84-9 1-(4-methanesulfonyloxy-3-methoxyphenyl)prop-2-en-1-ol 
• 32971-25-8 pinoresinol 
• 186581-53-3 diazomethane 
• 81446-29-9 (-)-pinoresinol 

Downstream Products

• 20610-45-1 (3aR)-1c,4t-bis-(2-bromo-4,5-dimethoxy-phenyl)-(3ar,6ac)-tetrahydro-furo[3,4-c]furan 
• 58311-18-5 (2R,3R)-2,3-bis[(3,4-dimethoxyphenyl)methyl]butane-1,4-diol 
• 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 
• 4375-03-5 (–)-eudesmin 
• 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 
• 487-39-8 (+)-pinoresinol monomethyl ether 
• 526-06-7 eudesmin 
• 20610-45-1 (3aS)-1c,4t-bis-(2-bromo-4,5-dimethoxy-phenyl)-(3ar,6ac)-tetrahydro-furo[3,4-c]furan 

Relevant articles and documents

Stereospecific synthesis of endo-endo-3,7-dioxabicyclo[3.3.0]octane lignans using 1,6-bis(dipropylboryl)-2,4-hexadiene

A general methodology for the stereoselective synthesis of compounds of the 2,6-diaryl-3,7-dioxabicyclo[3.3.0]octane series was developed. The strategy includes allylboration of aromatic aldehydes with 1,6-bis(dialkylboryl)-2,4- hexadiene, ozonolysis of the thus obtained 1,4-diaryl-2,3-divinyl-1,4-diols, and subsequent intramolecular cyclization. This methodology was used for obtaining the naturally occurring lignans of the furofuran series, viz., diaeudesmin, diayangambin, epiasarinin, epieudesmin, epiyangambin, and asarinin.

A Versatile Stereoselective Synthesis of endo,exo-Furofuranones: Application to the Enantioselective Synthesis of Furofuran Lignans

A new stereoselective route to endo,exo-2,6-diarylfurofuranones has been developed using Mn(III)-mediated intramolecular cyclopropanation and C-H insertion reactions as key C-C bond-forming steps. Mn(III)-mediated oxidative cyclization of acetoacetate derivative 11 afforded 1-acetyl-4-aryl-3-oxabicyclo[3.1.0]hexan-2-one (12) with excellent diastereocontrol (d.r. 22:1). Subsequent Lewis acid-catalyzed opening of the activated cyclopropane ring present in 12 with benzylic alcohols then gave α-acetyl-γ-butyrolactones 16 and 18-20, which reacted efficiently with in situ-generated TfN3 to secure the key α-diazo-γ -butyrolactones 22-25. Highly stereoselective rhodium-catalyzed C-H insertion reactions of diazolactones 22-25 completed the synthesis of endo,exo-2,6-diarylfurofuranones 26-29 in overall yields ranging from 41 to 48% from 1-phenylallyl alcohol (±)-10. The approach developed for the furofuranones 26-29 was then applied to the asymmetric syntheses of four furofuran lignans, (+)-xanthoxylol (1), (+)-methylxanthoxylol (2), (+)-epipinoresinol (3), and (+)-epieudesmin (4), starting from enantiomerically enriched 1-arylallyl alcohol (S)-31.

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.