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

Base Information

• Chemical Name: 5,7,3',4'-tetra-O-benzyl-[2-⁽¹³⁾C,4-⁽¹³⁾C]-(2R,3S)-catechin
• CAS No.: 1256496-71-5
• Molecular Formula: C₄₃H₃₈O₆
• Molecular Weight: 652.749
• Mol file: 1256496-71-5.mol

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

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

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,3S)-catechin

There total 9 articles about 5,7,3',4'-tetra-O-benzyl-[2-⁽¹³⁾C,4-⁽¹³⁾C]-(2R,3S)-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: 82.0%

[2-(13)C,4-(13)C]-3-O-propiolate ester-5,7,3',4'-tetra-O-benzyl-catechin → 5,7,3',4'-tetra-O-benzyl-[2-(13)C,4-(13)C]-(2R,3S)-catechin (1256496-71-5)

Guidance literature:

With potassium carbonate; In methanol; 1,2-dichloro-ethane; at 20 ℃; optical yield given as %ee;

DOI:10.1002/jlcr.1791

Reference yield:

[1-(13)C,3-(13)C]-3-(2,4-bis(benzyloxy)-6-hydroxyphenyl)-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 (1256496-71-5)

Guidance literature:

Multi-step reaction with 2 steps

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

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

With pyridinium p-toluenesulfonate; potassium carbonate; In methanol; 1,2-dichloro-ethane;

DOI:10.1002/jlcr.1791

Reference yield:

(E)-1-(2,4-bis(benzyloxy)-6-hydroxyphenyl)-3-(3',4'-bis(benzyloxy)phenyl)prop-2-(13)C-en-1-[(13)C]-one (1256496-59-9) → 5,7,3',4'-tetra-O-benzyl-[2-(13)C,4-(13)C]-(2R,3S)-catechin (1256496-71-5)

Guidance literature:

Multi-step reaction with 6 steps

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

2: 1H-imidazole / N,N-dimethyl-formamide / 20 h / 20 °C / Inert atmosphere

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

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

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

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

With 1H-imidazole; sodium tetrahydroborate; Hydroquinone 1,4-phthalazinediyl diether; methanesulfonamide; cerium(III) chloride heptahydrate; tetrabutyl ammonium fluoride; water; pyridinium p-toluenesulfonate; potassium carbonate; acetic acid; In tetrahydrofuran; methanol; ethanol; 1,2-dichloro-ethane; N,N-dimethyl-formamide; tert-butyl alcohol;

DOI:10.1002/jlcr.1791

upstream raw materials:

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

(E)-1-(2,4-bis(benzyloxy)-6-hydroxyphenyl)-3-(3',4'-bis(benzyloxy)phenyl)prop-2-⁽¹³⁾C-en-1-[⁽¹³⁾C]-one

3,5-dihydroxyphenol

3,4-bis(benzyloxy)benz-⁽¹³⁾C-aldehyde

Downstream raw materials:

[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

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

[2-⁽¹³⁾C,4-⁽¹³⁾C]-(2R,3R)-epicatechin

Refernces