80780-43-4

Usage

Molecular Weight

464.49 g/mol

Structure

The compound consists of two benzene rings, each substituted with three methoxy groups, connected by a tetrahydrofuran ring.

Class

It is a member of the furofuran class of organic compounds.

Applications

Often used in pharmaceutical research and synthesis.

Potential

Has potential applications in the development of new drugs.

Biological Activity

May exhibit biological activity due to its unique structure.

Relevance

Its properties and reactivity make it an interesting target for organic chemical research and synthesis.

Upstream product

• 487-35-4 (+)-syringaresinol 
• 77-78-1 dimethyl sulfate 
• 487-35-4 (+/-)-syringaresinol 
• 2373-80-0 3,4-methylenedioxy-trans-cinnamic acid 
• 20329-98-0 (E)-3,4,5-trimethoxy-cinnamic acid 
• 886989-84-0 (S)-1-[(E)-3-(3,4,5-trimethoxyphenyl)propenoyl]pyrrolidine-2-carboxylic acid 
• 886989-85-1 (1S,4S,5S,8S)-4,8-bis(3,4,5-trimethoxyphenyl)-3,7-dioxabicyclo[3.3.0]octane-2,6-dione 
• 886989-89-5 (1S,2R,3R,4S)-2,3-bis(hydroxymethyl)-1,4-bis(3,4,5-trimethoxyphenyl)butane-1,4-diol 

Downstream Products

• 24192-64-1 2,6-bis(3,4,5-trimethoxyphenyl)-3,7-dioxabicyclo[3.3.0]octane 
• 60619-98-9 (+)-syringaresinol dimethyl ether 

Relevant academic research and scientific papers

Electochemical asymmetric dimerization of cinnamic acid derivatives and application to the enantioselective syntheses of furofuran lignans

A new electrochemical method for the asymmetric oxidative dimerization of cinnamic acid derivatives has been developed. This method enabled the enantioselective syntheses of furofuran lignans, yangambin, sesamin and eudesmin.

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.

Simple and efficient asymmetric synthesis of furofuran lignans yangambin and caruilignan A

A novel asymmetric dimerization of cinnamic acid derivative was achieved in high efficiency and high stereoselectivity. By using the reaction as a key step, two furofuran lignans, yangambin and caruilignan A were synthesized in optically pure form in only 5 and 6 steps, respectively. Georg Thieme Verlag Stuttgart.

Photoinduced molecular transformations. 157. A new stereo- and regioselective synthesis of 2,6-diaryl-3,7-dioxabicyclo[3.3.0]octane lignans involving a β-scission of alkoxyl radicals as the key step. New total syntheses of (±)-sesamin, (±)-eudesmin, and (±)-yangambin

New total syntheses of naturally occurring 2,6-diaryl-3,7-dioxabicyclo[3.3.0]octane lignans, (±)-sesamin and (±)-eudesmin, and the first total synthesis of (±)-yangambin were achieved according to a general method devised by Suginome and colleagues for replacing the carbonyl group of the cyclopentanone ring with an oxygen atom to give a corresponding tetrahydrofuran ring involving a regioselective β-scission of alkoxyl radicals; arylation of dimethyl, diallyl, or dibenzyl 3,7-dioxobicyclo[3.3.0]octane-2,6-dicarbonate (18 and 19a,b) with aryllead triacetate 9a-c, followed by dealkoxycarbonylation of the resulting arylated product 20a-f, gave 2,6-diaryl-3,7-dioxobicyclo[3.3.0]octane 21a-c. A regioselective Baeyer-Villiger oxidation of 21a-c with m-CPBA-NaHCO3 or -K2CO3 gave the corresponding δ-lactone 22a-c, which was reduced with DIBAL to give the corresponding lactol 23a-c. The irradiation of a solution of the hypoiodite of 23a-c, generated in situ with mercury(II) oxide-iodine, in benzene with Pyrex-filtered light resulted in a regioselective β-scission of the corresponding alkoxyl radical to give iodo formate 24a-c. Heating 24a-c in MeOH with NaBH4 gave (±)-sesamin (25a), (±)-eudesmin (25b), or (±)-yangambin (25c).