(3S,4R,5R,6R)-3-(3,4,5-trimethoxy-α-hydroxybenzyl)-4-(3',4'-methylenedioxy-benzoyl)-5-(1-menthyloxy)butyrolactone

Base Information

• Chemical Name: (3S,4R,5R,6R)-3-(3,4,5-trimethoxy-α-hydroxybenzyl)-4-(3',4'-methylenedioxy-benzoyl)-5-(1-menthyloxy)butyrolactone
• CAS No.: 158752-81-9
• Molecular Formula: C₃₂H₄₀O₁₀
• Molecular Weight: 584.664
• Mol file: 158752-81-9.mol

Synonyms:(3S,4R,5R,6R)-3-(3,4,5-trimethoxy-α-hydroxybenzyl)-4-(3',4'-methylenedioxy-benzoyl)-5-(1-menthyloxy)butyrolactone

Chemical Property of (3S,4R,5R,6R)-3-(3,4,5-trimethoxy-α-hydroxybenzyl)-4-(3',4'-methylenedioxy-benzoyl)-5-(1-menthyloxy)butyrolactone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,4R,5R,6R)-3-(3,4,5-trimethoxy-α-hydroxybenzyl)-4-(3',4'-methylenedioxy-benzoyl)-5-(1-menthyloxy)butyrolactone

There total 4 articles about (3S,4R,5R,6R)-3-(3,4,5-trimethoxy-α-hydroxybenzyl)-4-(3',4'-methylenedioxy-benzoyl)-5-(1-menthyloxy)butyrolactone 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: 80.0%

(-)-(3S,4R,5R)-3-(3,4,5-trimethoxy-α-hydroxybenzyl)-4-(α--3',4'-methylenedioxyphenylacetonitrile)-5-(1-menthyloxy)butyrolactone → (3S,4R,5R,6R)-3-(3,4,5-trimethoxy-α-hydroxybenzyl)-4-(3',4'-methylenedioxy-benzoyl)-5-(1-menthyloxy)butyrolactone (158752-81-9)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at -78 ℃; for 0.25h;

DOI:10.1016/S0040-4020(01)89274-7

Reference yield:

(5R)-(L-menthyloxy)-2(5H)-furanone (112968-75-9,122079-41-8,122079-45-2,135041-07-5,77934-87-3) → (3S,4R,5R,6R)-3-(3,4,5-trimethoxy-α-hydroxybenzyl)-4-(3',4'-methylenedioxy-benzoyl)-5-(1-menthyloxy)butyrolactone (158752-81-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) diisopropylamine, n-BuLi / 2.) THF, 2 h; 3.) THF, 1 h

2: 80 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.25 h / -78 °C

With n-butyllithium; tetrabutyl ammonium fluoride; diisopropylamine; In tetrahydrofuran;

DOI:10.1016/S0040-4020(01)89274-7

Reference yield:

3,4,5-trimethoxy-benzaldehyde (86-81-7) → (3S,4R,5R,6R)-3-(3,4,5-trimethoxy-α-hydroxybenzyl)-4-(3',4'-methylenedioxy-benzoyl)-5-(1-menthyloxy)butyrolactone (158752-81-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) diisopropylamine, n-BuLi / 2.) THF, 2 h; 3.) THF, 1 h

2: 80 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.25 h / -78 °C

With n-butyllithium; tetrabutyl ammonium fluoride; diisopropylamine; In tetrahydrofuran;

DOI:10.1016/S0040-4020(01)89274-7

upstream raw materials:

(5R)-(L-menthyloxy)-2(5H)-furanone

3,4,5-trimethoxy-benzaldehyde

Benzo[1,3]dioxol-5-yl-(tert-butyl-dimethyl-silanyloxy)-acetonitrile

Downstream raw materials:

(-)-(3S,4R,5R,6R)-3-(3,4,5-trimethoxy-α-acetoxybenzyl)-4-(3',4'-methylenedioxybenzoyl)-5-(1-menthyloxy)butyrolactone