5,7,3',4'-tetra-O-benzyl-3-(3,4,5-tri-O-benzyl-galloyl)-epicatechin-(4β,8)-5,7,3',4'-tetra-O-benzyl-3-(3,4,5-tri-O-benzyl-galloyl)-epicatechin

Base Information

• Chemical Name: 5,7,3',4'-tetra-O-benzyl-3-(3,4,5-tri-O-benzyl-galloyl)-epicatechin-(4β,8)-5,7,3',4'-tetra-O-benzyl-3-(3,4,5-tri-O-benzyl-galloyl)-epicatechin
• CAS No.: 223387-33-5
• Molecular Formula: C₁₄₂H₁₁₈O₂₀
• Molecular Weight: 2144.49
• Mol file: 223387-33-5.mol

Synonyms:

Chemical Property of 5,7,3',4'-tetra-O-benzyl-3-(3,4,5-tri-O-benzyl-galloyl)-epicatechin-(4β,8)-5,7,3',4'-tetra-O-benzyl-3-(3,4,5-tri-O-benzyl-galloyl)-epicatechin

Chemical Property:

• Density: 1.34±0.1 g/cm3(Predicted)

Purity/Quality:

(2R,2''R,3R,3''R,4R)-2,2''-Bis[3,4-bis(phenylmethoxy)phenyl]-3,3'',4,4''-tetrahydro-5,5'',7,7''-tetrakis(phenylmethoxy)[4,8''-bi-2H-1-benzopyran]-3,3''-diylEster3,4,5-Tris(phenylmethoxy)-benzoicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: (2R,2''R,3R,3''R,4R)-2,2''-Bis[3,4-bis(phenylmethoxy)phenyl]-3,3'',4,4''-tetrahydro-5,5'',7,7''-tetrakis(phenylmethoxy)[4,8''-bi-2H-1-benzopyran]-3,3''-diyl Ester 3,4,5-Tris(phenylmethoxy)-benzoic Acid is an intermediate in the synthesis of Procyanidin B2 3,3''-Di-O-gallate (P755825). Procyanidin B2 3,3''-di-O-gallate is an important compound whose activity results in the inhibition of growth pertaining to human prostate carcinoma cell lines. Coming from the group of compounds known as flavonoids, Procyanidin B2 3,3''-di-O-gallate shows interesting biological activities relating to various human cancer diseases.

Technology Process of 5,7,3',4'-tetra-O-benzyl-3-(3,4,5-tri-O-benzyl-galloyl)-epicatechin-(4β,8)-5,7,3',4'-tetra-O-benzyl-3-(3,4,5-tri-O-benzyl-galloyl)-epicatechin

There total 9 articles about 5,7,3',4'-tetra-O-benzyl-3-(3,4,5-tri-O-benzyl-galloyl)-epicatechin-(4β,8)-5,7,3',4'-tetra-O-benzyl-3-(3,4,5-tri-O-benzyl-galloyl)-epicatechin 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: 99.0%

(2R,3R,4S)-5,7,3',4'-tetra-O-benzyl-4-(2''-ethoxyethoxy)flavan-3-yl (3''',4''',5'''-tri-O-benzyl)gallate (851775-46-7) + (-)-(2R,3R)-5,7-bis(benzyloxy)-2-[3,4-bis(benzyloxy)phenyl]chroman-3-yl 3,4,5-tris(benzyloxy)benzoate (256236-30-3) → 5,7,3',4'-tetra-O-benzyl-3-O-(3,4,5-tri-O-benzylgalloyl)-(-)-epicatechin-(4β,8β)-[5,7,3',4'-tetra-O-benzyl-3-O-(3,4,5-tri-O-benzylgalloyl)-(-)-epicatechin] (223387-33-5)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -20 ℃; for 0.0833333h;

DOI:10.1016/j.bmc.2005.02.023

Reference yield: 99.0%

(2R,3R,4S)-5,7,3',4'-tetra-O-benzyl-4-(2''-ethoxyethoxy)flavan-3-yl (3''',4''',5'''-tri-O-benzyl)gallate (851775-46-7) + (+)-(2R,3S)-5,7-bis(benzyloxy)-2-[3,4-bis(benzyloxy)phenyl]chroman-3-yl 3,4,5-tris(benzyloxy)benzoate (732298-13-4) → C142H118O20 (223387-33-5)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -10 ℃; for 0.0833333h;

DOI:10.1016/j.bmc.2005.02.023

Reference yield: 93.0%

(-)-(2R,3R)-5,7-bis(benzyloxy)-2-[3,4-bis(benzyloxy)phenyl]chroman-3-yl 3,4,5-tris(benzyloxy)benzoate (256236-30-3) + (2R,3S,4S)-5,7,3',4'-tetra-O-benzyl-4-(2''-ethoxyethoxy)flavan-3-yl (3'',4'',5''-tri-O-benzyl)gallate (828249-32-7) → [4,8]-2,3-trans-3,4-trans:2,3-cis-octa-O-benzyl-(+)-catechin-(-)-epicatechin-3,3''-di-O-(tri-O-benzyl)gallate (223387-33-5)

Guidance literature:

trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -20 ℃; for 0.0833333h;

DOI:10.3987/COM-05-S(T)11

upstream raw materials:

(+)-(2R,3S)-5,7-bis(benzyloxy)-2-[3,4-bis(benzyloxy)phenyl]chroman-3-yl 3,4,5-tris(benzyloxy)benzoate

(2R,3S,4S)-5,7,3',4'-tetra-O-benzyl-4-(2''-ethoxyethoxy)flavan-3-yl (3'',4'',5''-tri-O-benzyl)gallate

3,4,5-tribenzyloxybenzoic acid

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

Refernces

• 1、 Suda, Manato,Katoh, Miyuki,Toda, Kazuya,Matsumoto, Kiriko,Kawaguchi, Koichiro,Kawahara, Sei-Ichi,Hattori, Yasunao,Fujii, Hiroshi,Makabe, Hidefumi. "Syntheses of procyanidin B2 and B3 gallate derivatives using equimolar condensation mediated by Yb(OTf)3 and their antitumor activities". . p. 4935 - 4939. Retrieved 2013/09/02.
• 2、 -. "Processes for the preparation of protected-(+)-catechin and (-)-epicatechin monomers, for coupling the protected monomers with an activated, protected epicatechin monomer, and for the preparation of epicatechin-(4B,8)-epicatechin or -catechin dimers and their digallates". Page/Page column 7. . Retrieved 2010/11/25.