(7'S,8R,8'R)-4,7'-dihydroxy-3,3',4'-trimethoxylignano-9,9'-lactone

Base Information

• Chemical Name: (7'S,8R,8'R)-4,7'-dihydroxy-3,3',4'-trimethoxylignano-9,9'-lactone
• CAS No.: 74861-40-8
• Molecular Formula: C₂₁H₂₄O₇
• Molecular Weight: 388.417
• Mol file: 74861-40-8.mol

Synonyms:(7'S,8R,8'R)-4,7'-dihydroxy-3,3',4'-trimethoxylignano-9,9'-lactone

Chemical Property of (7'S,8R,8'R)-4,7'-dihydroxy-3,3',4'-trimethoxylignano-9,9'-lactone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (7'S,8R,8'R)-4,7'-dihydroxy-3,3',4'-trimethoxylignano-9,9'-lactone

There total 14 articles about (7'S,8R,8'R)-4,7'-dihydroxy-3,3',4'-trimethoxylignano-9,9'-lactone 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: 86.0%

(-)-(2S,5S)-4-[(tert-butyldimethylsilanyloxy)-(3,4-dimethoxyphenyl)methyl]-3-[4-(tert-butyldimethylsilanyloxy)-3-methoxybenzyl]dihydrofuran-2-one (689277-90-5) → (7'S,8R,8'R)-4,7'-dihydroxy-3,3',4'-trimethoxylignano-9,9'-lactone (74861-40-8)

Guidance literature:

With tetrabutyl ammonium fluoride; acetic acid; In tetrahydrofuran; at 20 ℃; for 336h;

DOI:10.1021/ol049878b

Reference yield: 65.0%

(8R,8'R)-4-tert-butyldimethylsilanyloxy-7'-hydroxy-3,3',4'-trimethoxylignano-9,9'-lactone → (7'S,8R,8'R)-4,7'-dihydroxy-3,3',4'-trimethoxylignano-9,9'-lactone (74861-40-8)

Guidance literature:

With tetrabutyl ammonium fluoride; acetic acid; In tetrahydrofuran; at 0 - 20 ℃; for 3.5h;

DOI:10.1039/b513303c

Reference yield:

Arctigenin (26687-82-1,81446-30-2,84413-77-4,87678-74-8,87678-75-9,144901-91-7,7770-78-7) → (7'S,8R,8'R)-4,7'-dihydroxy-3,3',4'-trimethoxylignano-9,9'-lactone (74861-40-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 340 mg / pyridine

2: 285 mg / acetic acid / 5 h / 70 - 80 °C

3: 53 mg / 4percent KOH / methanol

With potassium hydroxide; In pyridine; methanol; acetic acid;

upstream raw materials:

5-acetoxyisoarctigenin monoacetate

5-acetoxyarctigenin monoacetate

(-)-(2S,5S)-4-[(tert-butyldimethylsilanyloxy)-(3,4-dimethoxyphenyl)methyl]-3-[4-(tert-butyldimethylsilanyloxy)-3-methoxybenzyl]dihydrofuran-2-one

3,4-dimethoxy-benzaldehyde

Downstream raw materials:

Arctigenin

5-alloacetoxymatairesinol dimethyl ether

α-conidendrin dimethyl ether

isolariciresinol dimethyl ether