(2R,3S,4S)-3-acetoxy-5,7,3',4'-tetrabenzyloxy-4-(2-ethoxyethoxy)flavan

Base Information

• Chemical Name: (2R,3S,4S)-3-acetoxy-5,7,3',4'-tetrabenzyloxy-4-(2-ethoxyethoxy)flavan
• CAS No.: 664351-41-1
• Molecular Formula: C₄₉H₄₈O₉
• Molecular Weight: 780.915
• Mol file: 664351-41-1.mol

Synonyms:(2R,3S,4S)-3-acetoxy-5,7,3',4'-tetrabenzyloxy-4-(2-ethoxyethoxy)flavan

Chemical Property of (2R,3S,4S)-3-acetoxy-5,7,3',4'-tetrabenzyloxy-4-(2-ethoxyethoxy)flavan

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S,4S)-3-acetoxy-5,7,3',4'-tetrabenzyloxy-4-(2-ethoxyethoxy)flavan

There total 2 articles about (2R,3S,4S)-3-acetoxy-5,7,3',4'-tetrabenzyloxy-4-(2-ethoxyethoxy)flavan 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: 98.0%

acetic anhydride (108-24-7) + (2R,3S,4S)-5,7,3',4'-tetrabenzyloxy-4-(2-ethoxyethoxy)flavan-3-ol (478796-20-2) → (2R,3S,4S)-3-acetoxy-5,7,3',4'-tetrabenzyloxy-4-(2-ethoxyethoxy)flavan (664351-41-1)

Guidance literature:

With dmap; In dichloromethane;

DOI:10.1016/S0040-4020(02)00936-5

Reference yield:

5,7,3',4'-tetra-O-benzyl-(+)-catechin (20728-73-8) → (2R,3S,4S)-3-acetoxy-5,7,3',4'-tetrabenzyloxy-4-(2-ethoxyethoxy)flavan (664351-41-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 98 percent / DDQ / CH₂Cl₂ / 2 h / 20 °C

2: 98 percent / 4-(dimethylamino)pyridine / CH₂Cl₂

With dmap; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane;

DOI:10.1016/S0040-4020(02)00936-5

Reference yield: 100.0%

5,7,3',4'-tetra-O-benzyl-4α-(5,7,3',4'-tetra-O-benzylcatechin)catechin (137550-06-2) + (2R,3S,4S)-3-acetoxy-5,7,3',4'-tetrabenzyloxy-4-(2-ethoxyethoxy)flavan (664351-41-1) → C131H112O19

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -78 ℃;

DOI:10.1055/s-2004-822905

upstream raw materials:

acetic anhydride

(2R,3S,4S)-5,7,3',4'-tetrabenzyloxy-4-(2-ethoxyethoxy)flavan-3-ol

5,7,3',4'-tetra-O-benzyl-(+)-catechin

Downstream raw materials:

5,7,3',4'-tetra-O-benzyl-4β-(5,7,3',4'-tetra-O-benzylcatechin)catechin

5,7,3',4'-tetra-O-benzyl-4α-(5,7,3',4'-tetra-O-benzylcatechin)catechin

[4,8']-2,3-trans-3,4-trans:2',3'-trans-octa-O-benzyl-3-O-acetyl-bi-(+)-catechin

[4,8']-2,3-trans-3,4-trans:2',3'-cis-octa-O-benzyl-3-O-acetyl-(+)-catechin-(-)-epicatechin