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

Base Information

• Chemical Name: [4,8']-2,3-trans-3,4-trans:2',3'-trans-octa-O-benzyl-3-O-acetyl-bi-(+)-catechin
• CAS No.: 476312-06-8
• Molecular Formula: C₈₈H₇₆O₁₃
• Molecular Weight: 1341.56
• Mol file: 476312-06-8.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 10 articles about [4,8']-2,3-trans-3,4-trans:2',3'-trans-octa-O-benzyl-3-O-acetyl-bi-(+)-catechin 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: 75.0%

5,7,3',4'-tetra-O-benzyl-(+)-catechin (20728-73-8) + (2R,3S,4S)-5,7-bis(benzyloxy)-2-(3,4-bis(benzyloxy)phenyl)-4-(2-hydroxyethoxy)chroman-3-yl acetate → [4,8']-2,3-trans-3,4-trans:2',3'-trans-octa-O-benzyl-3-O-acetyl-bi-(+)-catechin (476312-06-8)

Guidance literature:

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

DOI:10.1016/j.bmcl.2017.10.007

Reference yield: 64.0%

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) → [4,8']-2,3-trans-3,4-trans:2',3'-trans-octa-O-benzyl-3-O-acetyl-bi-(+)-catechin (476312-06-8)

Guidance literature:

With ytterbium(III) triflate; In dichloromethane; at 20 ℃; for 2h;

DOI:10.1016/j.tetlet.2007.06.047

Reference yield: 60.0%

3,4-cis-4-acetoxy-3-O-acetyl-4-dehydro-5,7,3',4'-tetra-O-benzyl-(+)-catechin (478241-34-8) + 5,7,3',4'-tetra-O-benzyl-(+)-catechin (20728-73-8) → [4,8']-2,3-trans-3,4-trans:2',3'-trans-octa-O-benzyl-3-O-acetyl-bi-(+)-catechin (476312-06-8) + C133H114O20

Guidance literature:

With tris(pentafluorophenyl)borate; In dichloromethane; at 0 ℃; for 3.5h; Further Variations:; Reagents; Temperatures; time; Product distribution;

DOI:10.1016/j.tetlet.2008.02.173

upstream raw materials:

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

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

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

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

Downstream raw materials:

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

procyanidin B₃