(3R,4R)-3,4-bis(benzyloxy)-1-(4-methoxybenzyl)-pyrrolidine-2,5-dione

Base Information

• Chemical Name: (3R,4R)-3,4-bis(benzyloxy)-1-(4-methoxybenzyl)-pyrrolidine-2,5-dione
• CAS No.: 321566-90-9
• Molecular Formula: C₂₆H₂₅NO₅
• Molecular Weight: 431.488
• Mol file: 321566-90-9.mol

Synonyms:(3R,4R)-3,4-bis(benzyloxy)-1-(4-methoxybenzyl)-pyrrolidine-2,5-dione

Chemical Property of (3R,4R)-3,4-bis(benzyloxy)-1-(4-methoxybenzyl)-pyrrolidine-2,5-dione

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,4R)-3,4-bis(benzyloxy)-1-(4-methoxybenzyl)-pyrrolidine-2,5-dione

There total 6 articles about (3R,4R)-3,4-bis(benzyloxy)-1-(4-methoxybenzyl)-pyrrolidine-2,5-dione 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: 76.0%

(3R,4R)-3,4-bis(benzyloxy)-3,4-dihydro-2,5-furandione (97506-01-9) + 4-methoxy-benzylamine (2393-23-9) → (3R,4R)-3,4-bis(benzyloxy)-1-(4-methoxybenzyl)-pyrrolidine-2,5-dione (321566-90-9)

Guidance literature:

With acetyl chloride; In dichloromethane; at 0 ℃; for 5.25h; Reflux; Inert atmosphere;

DOI:10.1021/acs.joc.7b01814

Reference yield:

diethyl (2R,3R)-2,3-bis(benzyloxy)butane-1,4-dioate (77312-71-1) → (3R,4R)-3,4-bis(benzyloxy)-1-(4-methoxybenzyl)-pyrrolidine-2,5-dione (321566-90-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: LiOH / ethanol; H₂O / 0 - 5 °C

2.1: acetyl chloride / 4 h / Heating

2.2: CH₂Cl₂ / 5 h / Heating

2.3: acetyl chloride / 6 h / Heating

With lithium hydroxide; acetyl chloride; In ethanol; water;

DOI:10.1016/j.tet.2007.02.087

Reference yield:

(2R,3R)-2,3-bis(benzyloxy)tartaric acid (138794-81-7) → (3R,4R)-3,4-bis(benzyloxy)-1-(4-methoxybenzyl)-pyrrolidine-2,5-dione (321566-90-9)

Guidance literature:

Multi-step reaction with 2 steps

1: acetyl chloride / 4 h / Reflux; Inert atmosphere

2: acetyl chloride / dichloromethane / 5.25 h / 0 °C / Reflux; Inert atmosphere

With acetyl chloride; In dichloromethane;

DOI:10.1021/acs.joc.7b01814

upstream raw materials:

(2R,3R)-2,3-bis(benzyloxy)tartaric acid

4-methoxy-benzylamine

diethyl (2R,3R)-2,3-bis(benzyloxy)butane-1,4-dioate

(3R,4R)-3,4-bis(benzyloxy)-3,4-dihydro-2,5-furandione

Downstream raw materials:

(3R,4R)-3,4-bis(benzyloxy)pyrrolidine-2,5-dione

(3R,4R,5R)-1-allyl-3,4-bis(benzyloxy)-5-(difluoro(phenylthio)methyl)-5-hydroxypyrrolidin-2-one

(3R,4R,5S)-1-allyl-3,4-bis(benzyloxy)-5-(difluoro(phenylthio)methyl)-5-hydroxypyrrolidin-2-one

(3R,4R,5R)-3,4-bis(benzyloxy)-1-(but-3-enyl)-5-(difluoro(phenylthio)methyl)-5-hydroxypyrrolidin-2-one