6383-02-4

Usage

Uses

Used in Pharmaceutical Industry:
2,4-bis(benzyloxy)-1-methoxybenzene is used as a reactant in the synthesis of Lamellarin D, a potent inhibitor of topoisomerase. 2,4-bis(benzyloxy)-1-methoxybenzene has potential applications in the development of anticancer drugs, as topoisomerase inhibitors are known to interfere with the replication and transcription of DNA in cancer cells, leading to their death.
Additionally, 2,4-bis(benzyloxy)-1-methoxybenzene can be utilized in the synthesis of other bioactive compounds with potential therapeutic applications, making it a valuable building block in the pharmaceutical industry. Its versatility in chemical reactions and ability to form various derivatives make it a promising candidate for further research and development in drug discovery.

Upstream product

• 6195-80-8 2,4-bis(benzyloxy)phenol 
• 74-88-4 methyl iodide 
• 100-44-7 benzyl chloride 
• 84354-17-6 2-methoxy-5-benzyloxyphenol 
• 30485-15-5 (+/-)-4,5,6-Tribenzyloxycyclohex-2-enon 
• 30485-14-4 (+/-)-3,4,5,6-Tetrakisbenzyloxy-cyclohex-2-enol 
• 29847-13-0 (±)-1,4,5,6-tetra-O-benzyl-2,3-O-isopropylidene-myo-inositol 
• 40914-19-0 3-benzyloxy-4-methoxyphenol 
• 100-39-0 benzyl bromide 
• 369371-92-6 acetic acid 5-benzyloxy-2-methoxy-phenyl ester 
• 67978-81-8 5-benzyloxy-2-methoxyacetophenone 

Downstream Products

• 680189-50-8 2-(2,4-dihydroxy-5-methoxy-phenyl)-8-hydroxy-1-(3-hydroxy-4-methoxy-phenyl)-9-methoxy-5,6-dihydro-pyrrolo[2,1-a]isoquinoline-3-carboxylic acid ethyl ester 
• 149355-76-0 14-(3,4-dimethoxyphenyl)-3,11-dihydroxy-2,12-dimethoxy-8,9-dihydro-6H-chromeno[4',3':4,5]pyrrolo[2,1-a]isoquinolin-6-one 
• 919082-36-3 ethyl 8-(benzyloxy)-2-(2,4-bis(benzyloxy)-5-methoxyphenyl)-1-(3,4-dimethoxyphenyl)-9-methoxy-5,6-dihydropyrrolo[2,1-a]-isoquinoline-3-carboxylate 
• 149378-57-4 3,11-dihydroxy-14-(3-hydroxy-4-methoxyphenyl)-2,12-dimethoxy-8,9-dihydro-6H-[1]benzopyrano-[4′,3′:4,5]pyrrolo-[2,1-a]isoquinolin-6-one 
• 680189-48-4 ethyl 8-(benzyloxy)-1-(3-(benzyloxy)-4-methoxyphenyl)-2-(2,4-bis(benzyloxy)-5-methoxyphenyl)-9-methoxy-5,6-dihydropyrrolo-[2,1-a]isoquinoline-3-carboxylate 
• 67978-82-9 Acetic acid 3,5-bis-benzyloxy-2-[(E)-3-(2,4-bis-benzyloxy-5-methoxy-phenyl)-acryloyl]-phenyl ester 
• 7298-50-2 2,4-bis-(benzyloxy)-5-methoxybenzaldehyde 
• 6100-60-3 4-methoxybenzene-1,3-diol 

Relevant academic research and scientific papers

Total Synthesis of Lamellarins G, J, L, and Z Using One-Pot Halogen Dance/Negishi Coupling

A bottom-up synthesis of lamellarins G, J, L, and Z was achieved via one-pot halogen dance/Negishi coupling of a lithiated dibromopyrrole derivative. The easily accessible dibromopyrrole bearing an ester moiety underwent halogen dance smoothly at -78 °C within 10 min. The resultant α-pyrrolyllithium was transmetalated to the corresponding organozinc species, which was then coupled with an aryl iodide in the presence of catalytic palladium to provide the fully substituted pyrrole. Subsequent halogen-lithium exchange was performed to incorporate a boronate group exclusively at the β position proximal to the ester moiety. This synthetic intermediate allowed stepwise diarylation for the total synthesis of lamellarins G, J, L, and Z.

Synthesis of lamellarin U and lamellarin G trimethyl ether by alkylation of a deprotonated α-aminonitrile

(Chemical Equation Presented) 1,2,3,4-Tetrahydroisoquinoline-1- carbonitriles can serve as starting materials for the one-pot synthesis of 5,6-dihydropyrrolo[2,1a]isoquinolines and 1-benzyl-3,4-dihydroisoquinolines. The latter compounds were transformed to lamellarin G trimethyl ether and lamellarin U in short reaction sequences. This method allows the introduction of acid-sensitive protecting groups for the phenolic hydroxy functions which would be cleaved under the harsh conditions of the classical Bischler-Napieralski reaction.

Facile synthesis of polyhydroxycoumaronochromones with quinones: Synthesis of alkylpolyhydroxy- and alkoxycoumaronochromones from 2′-hydroxyisoflavones

4′,5,7-Trihydroxy- or 8-alkyl-4′,5,7-trihydroxycoumaronochromones were synthesized by oxidative cyclization of the corresponding 2′-hydroxyisoflavones with o-chloranil under mild conditions. By contrast, alkoxycoumaronochromones were synthesized by oxidative cyclization of the corresponding 2′-hydroxyisoflavones with DDQ.