5,7,3',4'-tetra-O-benzyl-[2-⁽¹³⁾C,4-⁽¹³⁾C]-(2R,3R)-epicatechin

Base Information

• Chemical Name: 5,7,3',4'-tetra-O-benzyl-[2-⁽¹³⁾C,4-⁽¹³⁾C]-(2R,3R)-epicatechin
• CAS No.: 1256496-81-7
• Molecular Formula: C₄₃H₃₈O₆
• Molecular Weight: 652.749
• Mol file: 1256496-81-7.mol

Synonyms:5,7,3',4'-tetra-O-benzyl-[2-⁽¹³⁾C,4-⁽¹³⁾C]-(2R,3R)-epicatechin

Chemical Property of 5,7,3',4'-tetra-O-benzyl-[2-⁽¹³⁾C,4-⁽¹³⁾C]-(2R,3R)-epicatechin

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5,7,3',4'-tetra-O-benzyl-[2-⁽¹³⁾C,4-⁽¹³⁾C]-(2R,3R)-epicatechin

There total 12 articles about 5,7,3',4'-tetra-O-benzyl-[2-⁽¹³⁾C,4-⁽¹³⁾C]-(2R,3R)-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: 74.0%

(2R)-[2-(13)C,4-(13)C]-5,7-bis(benzyloxy)-2-(3',4'-bis(benzyloxy)chroman)-3-one (1256496-78-2) → 5,7,3',4'-tetra-O-benzyl-[2-(13)C,4-(13)C]-(2R,3R)-epicatechin (1256496-81-7)

Guidance literature:

With aluminum isopropoxide; isopropyl alcohol; In toluene; at 110 - 115 ℃; optical yield given as %ee; Inert atmosphere;

DOI:10.1002/jlcr.1791

Reference yield:

(1S,2S)-[1-(13)C,3-(13)C]-3-(2,4-bis(benzyloxy)-6-(tert-butyldimethylsilyloxy)phenyl)-1-(3',4'-bis(benzyloxy)phenyl)propane-1,2-diol (1256496-65-7) → 5,7,3',4'-tetra-O-benzyl-[2-(13)C,4-(13)C]-(2R,3R)-epicatechin (1256496-81-7)

Guidance literature:

Multi-step reaction with 5 steps

1: tetrabutyl ammonium fluoride; acetic acid / tetrahydrofuran / 0.5 h / 0 - 5 °C / Inert atmosphere

2: pyridinium p-toluenesulfonate / 1,2-dichloro-ethane / Heating

3: potassium carbonate / methanol; 1,2-dichloro-ethane / 20 °C

4: Dess-Martin periodane / dichloromethane; water / 2 h / 20 °C / Inert atmosphere

5: aluminum isopropoxide; isopropyl alcohol / toluene / 110 - 115 °C / Inert atmosphere

With tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; aluminum isopropoxide; potassium carbonate; Dess-Martin periodane; acetic acid; isopropyl alcohol; In tetrahydrofuran; methanol; dichloromethane; water; 1,2-dichloro-ethane; toluene; 5: Meerwein-Ponndorf-Verley reduction;

DOI:10.1002/jlcr.1791

Reference yield:

1-[13C]-2',4',6'-trihydroxyacetophenone (1256496-52-2) → 5,7,3',4'-tetra-O-benzyl-[2-(13)C,4-(13)C]-(2R,3R)-epicatechin (1256496-81-7)

Guidance literature:

Multi-step reaction with 10 steps

1.1: potassium carbonate / N,N-dimethyl-formamide / 35 - 55 °C / Inert atmosphere

2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 5 °C / Inert atmosphere

2.2: 5 - 20 °C / Inert atmosphere

3.1: sodium tetrahydroborate; cerium(III) chloride heptahydrate / tetrahydrofuran; ethanol / 0 - 4 °C

4.1: 1H-imidazole / N,N-dimethyl-formamide / 20 h / 20 °C / Inert atmosphere

5.1: Hydroquinone 1,4-phthalazinediyl diether; methanesulfonamide; water / N,N-dimethyl-formamide; tert-butyl alcohol / 42 h / 0 - 10 °C / Inert atmosphere

6.1: tetrabutyl ammonium fluoride; acetic acid / tetrahydrofuran / 0.5 h / 0 - 5 °C / Inert atmosphere

7.1: pyridinium p-toluenesulfonate / 1,2-dichloro-ethane / Heating

8.1: potassium carbonate / methanol; 1,2-dichloro-ethane / 20 °C

9.1: Dess-Martin periodane / dichloromethane; water / 2 h / 20 °C / Inert atmosphere

10.1: aluminum isopropoxide; isopropyl alcohol / toluene / 110 - 115 °C / Inert atmosphere

With 1H-imidazole; sodium tetrahydroborate; Hydroquinone 1,4-phthalazinediyl diether; methanesulfonamide; cerium(III) chloride heptahydrate; tetrabutyl ammonium fluoride; water; pyridinium p-toluenesulfonate; aluminum isopropoxide; sodium hydride; potassium carbonate; Dess-Martin periodane; acetic acid; isopropyl alcohol; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide; toluene; mineral oil; tert-butyl alcohol; 10.1: Meerwein-Ponndorf-Verley reduction;

DOI:10.1002/jlcr.1791

upstream raw materials:

(1S,2S)-[1-⁽¹³⁾C,3-⁽¹³⁾C]-3-(2,4-bis(benzyloxy)-6-(tert-butyldimethylsilyloxy)phenyl)-1-(3',4'-bis(benzyloxy)phenyl)propane-1,2-diol

5,7,3',4'-tetra-O-benzyl-[2-⁽¹³⁾C,4-⁽¹³⁾C]-(2R,3S)-catechin

(2R)-[2-⁽¹³⁾C,4-⁽¹³⁾C]-5,7-bis(benzyloxy)-2-(3',4'-bis(benzyloxy)chroman)-3-one

1-[¹³C]-2',4',6'-trihydroxyacetophenone

Downstream raw materials:

[2-⁽¹³⁾C,4-⁽¹³⁾C]-(2R,3R)-epicatechin

Refernces