(+/-)-trans-2-(4-benzyloxy-3,5-dimethoxybenzyl)-3-piperonyl-4-butanolide

Base Information

• Chemical Name: (+/-)-trans-2-(4-benzyloxy-3,5-dimethoxybenzyl)-3-piperonyl-4-butanolide
• CAS No.: 131523-35-8
• Molecular Formula: C₂₈H₂₈O₇
• Molecular Weight: 476.526
• Mol file: 131523-35-8.mol

Synonyms:(+/-)-trans-2-(4-benzyloxy-3,5-dimethoxybenzyl)-3-piperonyl-4-butanolide

Chemical Property of (+/-)-trans-2-(4-benzyloxy-3,5-dimethoxybenzyl)-3-piperonyl-4-butanolide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+/-)-trans-2-(4-benzyloxy-3,5-dimethoxybenzyl)-3-piperonyl-4-butanolide

There total 9 articles about (+/-)-trans-2-(4-benzyloxy-3,5-dimethoxybenzyl)-3-piperonyl-4-butanolide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 84.0%

benzyl bromide (100-39-0) + rac-(8α,8'β)-4'-hydroxy-3',5'-dimethoxy-3,4-methylenedioxylignan-9',9-olide (119030-80-7) → (+/-)-trans-2-(4-benzyloxy-3,5-dimethoxybenzyl)-3-piperonyl-4-butanolide (131523-35-8)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; at 55 ℃; for 6h;

DOI:10.1248/cpb.38.1898

Reference yield: 67.0%

4-(1,3-benzodioxol-5-ylmethyl)-4,5-dihydrofuran-2(3H)-one (80483-34-7) + 2-(benzyloxy)-5-(bromomethyl)-1,3-dimethoxybenzene (111194-05-9) → (+/-)-trans-2-(4-benzyloxy-3,5-dimethoxybenzyl)-3-piperonyl-4-butanolide (131523-35-8)

Guidance literature:

With lithium hexamethyldisilazane; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; at 0 ℃;

DOI:10.1016/S0031-9422(00)89595-3

Reference yield:

piperonal (120-57-0,30024-74-9) → (+/-)-trans-2-(4-benzyloxy-3,5-dimethoxybenzyl)-3-piperonyl-4-butanolide (131523-35-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) lithium methylate, 2.) H₂, 3.) CaBH₄, 4.) aq. HCl / 2.) Pd-C / 1) MeOH, reflux; 2) MeOH, room temperature; 3) THF, room temperature; 4) EtOAc, room temperature

2: 67 percent / lithium hexamethyldisilazane / tetrahydrofuran; hexamethylphosphoric acid triamide / 0 °C

With hydrogenchloride; lithium methanolate; hydrogen; lithium hexamethyldisilazane; palladium on activated charcoal; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide;

DOI:10.1016/S0031-9422(00)89595-3

upstream raw materials:

benzyl bromide

rac-(8α,8'β)-4'-hydroxy-3',5'-dimethoxy-3,4-methylenedioxylignan-9',9-olide

4-(1,3-benzodioxol-5-ylmethyl)-4,5-dihydrofuran-2(3H)-one

2-(benzyloxy)-5-(bromomethyl)-1,3-dimethoxybenzene

Downstream raw materials:

(+/-)-10-benzyloxyisostegane

rac-(8α,8'β)-4'-hydroxy-3',5'-dimethoxy-3,4-methylenedioxylignan-9',9-olide