(S)-(E)-(4-benzyloxy-3,5-dimethoxybenzylidene)-3-(3,4,5-trimethoxybenzyl)butanolide

Base Information

• Chemical Name: (S)-(E)-(4-benzyloxy-3,5-dimethoxybenzylidene)-3-(3,4,5-trimethoxybenzyl)butanolide
• CAS No.: 167950-05-2
• Molecular Formula: C₃₀H₃₂O₈
• Molecular Weight: 520.579
• Mol file: 167950-05-2.mol

Synonyms:(S)-(E)-(4-benzyloxy-3,5-dimethoxybenzylidene)-3-(3,4,5-trimethoxybenzyl)butanolide

Chemical Property of (S)-(E)-(4-benzyloxy-3,5-dimethoxybenzylidene)-3-(3,4,5-trimethoxybenzyl)butanolide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-(E)-(4-benzyloxy-3,5-dimethoxybenzylidene)-3-(3,4,5-trimethoxybenzyl)butanolide

There total 3 articles about (S)-(E)-(4-benzyloxy-3,5-dimethoxybenzylidene)-3-(3,4,5-trimethoxybenzyl)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:

(S)-3-methoxycarbonyl-4-(3,4,5-trimethoxy-phenyl)butanoic acid (133269-68-8) → (S)-(E)-(4-benzyloxy-3,5-dimethoxybenzylidene)-3-(3,4,5-trimethoxybenzyl)butanolide (167950-05-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 201 g / KOH, CaCl₂, NaBH₄ / ethanol / 12 h / 0 °C

With potassium hydroxide; sodium tetrahydroborate; calcium chloride; In ethanol;

DOI:10.1016/0040-4020(95)00702-A

Reference yield:

(E)-3-(methoxycarbonyl)-4-(3,4,5-trimethoxy-phenyl)but-3-enoic acid (165673-39-2) → (S)-(E)-(4-benzyloxy-3,5-dimethoxybenzylidene)-3-(3,4,5-trimethoxybenzyl)butanolide (167950-05-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 250 g / Rh(COD)2BF₄, (R,R)-MOD-DIOP, Et₃N, hydrogen / methanol / 42 h / Ambient temperature

2: 201 g / KOH, CaCl₂, NaBH₄ / ethanol / 12 h / 0 °C

With potassium hydroxide; sodium tetrahydroborate; rhodium(I)-bis(1,5-cyclooctadiene) tetrafluoroborate; hydrogen; (4R-trans)-<(2,2-dimethyl-1,3-dioxolane-4,5-diyl)bis(methylene)>bis; triethylamine; calcium chloride; In methanol; ethanol;

DOI:10.1016/0040-4020(95)00702-A

Reference yield:

4-(benzyloxy)-3,5-dimethoxybenzaldehyde (6527-32-8) + (S)-dihydro-4-(3,4,5-trimethoxybenzyl)furan-2(3H)-one (143616-19-7) → (S)-(E)-(4-benzyloxy-3,5-dimethoxybenzylidene)-3-(3,4,5-trimethoxybenzyl)butanolide (167950-05-2)

Guidance literature:

Yield given. Multistep reaction;

DOI:10.1016/0040-4020(95)00702-A

upstream raw materials:

4-(benzyloxy)-3,5-dimethoxybenzaldehyde

(S)-dihydro-4-(3,4,5-trimethoxybenzyl)furan-2(3H)-one

(S)-3-methoxycarbonyl-4-(3,4,5-trimethoxy-phenyl)butanoic acid

(E)-3-(methoxycarbonyl)-4-(3,4,5-trimethoxy-phenyl)but-3-enoic acid