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

Base Information

• Chemical Name: (-)-(3S,4R,5R,6R)-3-(3,4,5-trimethoxy-α-acetoxybenzyl)-4-(3',4'-methylenedioxybenzoyl)-5-(1-menthyloxy)butyrolactone
• CAS No.: 158752-82-0
• Molecular Formula: C₃₄H₄₂O₁₁
• Molecular Weight: 626.701
• Mol file: 158752-82-0.mol

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

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

There total 5 articles about (-)-(3S,4R,5R,6R)-3-(3,4,5-trimethoxy-α-acetoxybenzyl)-4-(3',4'-methylenedioxybenzoyl)-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: 91.0%

acetic anhydride (108-24-7) + (3S,4R,5R,6R)-3-(3,4,5-trimethoxy-α-hydroxybenzyl)-4-(3',4'-methylenedioxy-benzoyl)-5-(1-menthyloxy)butyrolactone (158752-81-9) → (-)-(3S,4R,5R,6R)-3-(3,4,5-trimethoxy-α-acetoxybenzyl)-4-(3',4'-methylenedioxybenzoyl)-5-(1-menthyloxy)butyrolactone (158752-82-0)

Guidance literature:

With dmap; In dichloromethane; for 2h;

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-acetoxybenzyl)-4-(3',4'-methylenedioxybenzoyl)-5-(1-menthyloxy)butyrolactone (158752-82-0)

Guidance literature:

Multi-step reaction with 3 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

3: 91 percent / DMAP / CH₂Cl₂ / 2 h

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

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-acetoxybenzyl)-4-(3',4'-methylenedioxybenzoyl)-5-(1-menthyloxy)butyrolactone (158752-82-0)

Guidance literature:

Multi-step reaction with 3 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

3: 91 percent / DMAP / CH₂Cl₂ / 2 h

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

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

upstream raw materials:

acetic anhydride

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

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

3,4,5-trimethoxy-benzaldehyde