(3R,4R)-3-(3,4-dimethoxybenzyl)-4-(4-hydroxy-3-methoxybenzyl)tetrahydrofuran

Base Information

• Chemical Name: (3R,4R)-3-(3,4-dimethoxybenzyl)-4-(4-hydroxy-3-methoxybenzyl)tetrahydrofuran
• CAS No.: 119069-38-4
• Molecular Formula: C₂₁H₂₆O₅
• Molecular Weight: 358.434
• Mol file: 119069-38-4.mol

Synonyms:(3R,4R)-3-(3,4-dimethoxybenzyl)-4-(4-hydroxy-3-methoxybenzyl)tetrahydrofuran

Chemical Property of (3R,4R)-3-(3,4-dimethoxybenzyl)-4-(4-hydroxy-3-methoxybenzyl)tetrahydrofuran

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,4R)-3-(3,4-dimethoxybenzyl)-4-(4-hydroxy-3-methoxybenzyl)tetrahydrofuran

There total 3 articles about (3R,4R)-3-(3,4-dimethoxybenzyl)-4-(4-hydroxy-3-methoxybenzyl)tetrahydrofuran 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: 95.0%

(2R,3R)-2-(4-hydroxy-3-methoxybenzyl)-3-(3,4-dimethoxybenzyl)-1,4-butanediol (73354-08-2) → (3R,4R)-3-(3,4-dimethoxybenzyl)-4-(4-hydroxy-3-methoxybenzyl)tetrahydrofuran (119069-38-4)

Guidance literature:

With toluene-4-sulfonic acid; In dichloromethane; for 168h; Inert atmosphere; Reflux;

DOI:10.1039/d1ob01653a

Reference yield: 81.0%

Arctigenin (26687-82-1,81446-30-2,84413-77-4,87678-74-8,87678-75-9,144901-91-7,7770-78-7) → (3R,4R)-3-(3,4-dimethoxybenzyl)-4-(4-hydroxy-3-methoxybenzyl)tetrahydrofuran (119069-38-4)

Guidance literature:

Arctigenin; With sodium tetrahydroborate; boron trifluoride diethyl etherate; In tetrahydrofuran; at 0 - 20 ℃; for 3h;

With toluene-4-sulfonic acid; In dichloromethane; for 1h; Reflux;

DOI:10.1016/j.bmc.2013.04.010

Reference yield:

(3R,4R)-3-[(3-methoxy-4-benzyloxyphenyl)methyl]-4-[(3,4-dimethoxyphenyl)methyl] dihydro-2-(3H)-furanone (123251-05-8) → (3R,4R)-3-(3,4-dimethoxybenzyl)-4-(4-hydroxy-3-methoxybenzyl)tetrahydrofuran (119069-38-4)

Guidance literature:

Multi-step reaction with 3 steps

1: palladium 10% on activated carbon; hydrogen / ethanol / 0.5 h

2: lithium borohydride / tetrahydrofuran / Inert atmosphere; Reflux

3: toluene-4-sulfonic acid / dichloromethane / 168 h / Inert atmosphere; Reflux

With lithium borohydride; palladium 10% on activated carbon; hydrogen; toluene-4-sulfonic acid; In tetrahydrofuran; ethanol; dichloromethane;

DOI:10.1039/d1ob01653a

upstream raw materials:

(2R,3R)-2-(4-hydroxy-3-methoxybenzyl)-3-(3,4-dimethoxybenzyl)-1,4-butanediol

Arctigenin

(3R,4R)-3-[(3-methoxy-4-benzyloxyphenyl)methyl]-4-[(3,4-dimethoxyphenyl)methyl] dihydro-2-(3H)-furanone

Downstream raw materials:

C₂₈H₃₆O₆

C₂₉H₃₂F₂O₅

C₂₈H₃₃NO₅

C₃₀H₃₇NO₅