119030-80-7

Upstream product

• 131523-34-7 (+/-)-trans-2-(4-Benzyloxy-3,5-dimethoxybenzyl)-3-(3,4-methylenedioxy)-α,α-bis(phenylthio)benzylbutanolide 
• 17301-91-6 (3R*,4R*)-3-(3,4,5-trimethoxybenzyl)-4-(3,4-methylenedioxybenzyl)-4,5-dihydro-2(3H)-furanone 
• 141-78-6 ethyl acetate 
• 2176-18-3 4-benzyloxy-3,5-dimethoxybenzyl alcohol 
• 134-96-3 syringic aldehyde 
• 119030-77-2 4-benzyloxy-3,5-dimethoxybenzyl alcohol 
• 119030-76-1 4-benzyloxy-3,5-dimethoxybenzaldehyde 
• 69146-92-5 4-benzoyloxy-3,5-dimethoxybenzyl bromide 
• 111194-05-9 2-(benzyloxy)-5-(bromomethyl)-1,3-dimethoxybenzene 
• 80483-34-7 4-(1,3-benzodioxol-5-ylmethyl)-4,5-dihydrofuran-2(3H)-one 
• 120-57-0 piperonal 
• 131523-35-8 (+/-)-trans-2-(4-benzyloxy-3,5-dimethoxybenzyl)-3-piperonyl-4-butanolide 
• 119030-79-4 rac-(8α,8'β)-4'-benzoyloxy-3',5'-dimethoxy-3,4-methylenedioxylignan-9',9-olide 

Downstream Products

• 131523-36-9 (+/-)-10-benzyloxyisostegane 
• 131523-35-8 (+/-)-trans-2-(4-benzyloxy-3,5-dimethoxybenzyl)-3-piperonyl-4-butanolide 

Relevant academic research and scientific papers

Synthesis, antitumoral and antiviral evaluation of halo- and demethyl-yatein derivatives

Several chloro- and iodo-lignanolides have been obtained by direct halogenation of aromatic rings from yatein and 4'-O-demethylyatein. They were assayed as antineoplastics, in order to check the influence in the activity of substitution in both aromatic rings. Although these compounds show a modest antineoplastic activity, it is far from that displayed by yatein and podophyllotoxin. These results confirm that demethylation and the introduction of halo substituents diminish the activity of lignans of the dibenzylbutyrolactone type.

Oxygen-Free Regioselective Biocatalytic Demethylation of Methyl-phenyl Ethers via Methyltransfer Employing Veratrol- O-demethylase

The cleavage of aryl methyl ethers is a common reaction in chemistry requiring rather harsh conditions; consequently, it is prone to undesired reactions and lacks regioselectivity. Nevertheless, O-demethylation of aryl methyl ethers is a tool to valorize natural and pharmaceutical compounds by deprotecting reactive hydroxyl moieties. Various oxidative enzymes are known to catalyze this reaction at the expense of molecular oxygen, which may lead in the case of phenols/catechols to undesired side reactions (e.g., oxidation, polymerization). Here an oxygen-independent demethylation via methyl transfer is presented employing a cobalamin-dependent veratrol-O-demethylase (vdmB). The biocatalytic demethylation transforms a variety of aryl methyl ethers with two functional methoxy moieties either in 1,2-position or in 1,3-position. Biocatalytic reactions enabled, for instance, the regioselective monodemethylation of substituted 3,4-dimethoxy phenol as well as the monodemethylation of 1,3,5-trimethoxybenzene. The methyltransferase vdmB was also successfully applied for the regioselective demethylation of natural compounds such as papaverine and rac-yatein. The approach presented here represents an alternative to chemical and enzymatic demethylation concepts and allows performing regioselective demethylation in the absence of oxygen under mild conditions, representing a valuable extension of the synthetic repertoire to modify pharmaceuticals and diversify natural products.

Oxidative Coupling of Lignans. IV. Monophenolic Oxidative Coupling

Oxidative coupling of the monophenolic monoester (6) gives an aryltetralin (12) which is a potential intermediate for the synthesis of clinically active monophenolic lignan lactones.In contrast, oxidative couplings of the monophenols (32) and (35), derived from matairesinol (29), give mixtures of diastereoisomeric cyclooctadiene lignans while 4'-demethyldeoxypodorhizon (26) does not cyclize.These results show that the degree of aromatic substitution in monophenolic diarylbutanes plays an important role in determining the outcome of oxidative coupling.An alternative synthesis of the lactone (57) from piperonal has been investigated.