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

Base Information

• Chemical Name: (2R,3S,4S)-5,7,3',4'-tetrabenzyloxy-3-acetoxy-4-methoxyflavan
• CAS No.: 476312-04-6
• Molecular Formula: C₄₆H₄₂O₈
• Molecular Weight: 722.835
• Mol file: 476312-04-6.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 2 articles about (2R,3S,4S)-5,7,3',4'-tetrabenzyloxy-3-acetoxy-4-methoxyflavan 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: 97.0%

acetic anhydride (108-24-7) + (2R,3S,4S)-5,7,3',4'-tetrabenzyloxy-4-methoxyflavan-3-ol (294203-72-8) → (2R,3S,4S)-5,7,3',4'-tetrabenzyloxy-3-acetoxy-4-methoxyflavan (476312-04-6)

Guidance literature:

With dmap; In pyridine; at 20 ℃; for 1h;

DOI:10.1271/bbb.66.1764

Reference yield:

5,7,3',4'-tetra-O-benzyl-(+)-catechin (20728-73-8) → (2R,3S,4S)-5,7,3',4'-tetrabenzyloxy-3-acetoxy-4-methoxyflavan (476312-04-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 42 percent / DDQ / CH₂Cl₂

2: 97 percent / DMAP / pyridine / 1 h / 20 °C

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

DOI:10.1271/bbb.66.1764

Reference yield: 86.0%

5,7,3',4'-tetra-O-benzyl-4α-(5,7,3',4'-tetra-O-benzylcatechin)catechin (137550-06-2) + (2R,3S,4S)-5,7,3',4'-tetrabenzyloxy-3-acetoxy-4-methoxyflavan (476312-04-6) → C131H112O19

Guidance literature:

With silver trifluoromethanesulfonate; In dichloromethane; at 20 ℃; for 3h; diastereoselective reaction;

DOI:10.3987/COM-11-12159

upstream raw materials:

acetic anhydride

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

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

Downstream raw materials:

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

procyanidin B₃

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