3-(3,4-Dimethoxy-phenyl)-3-oxo-propionic acid (1R,2S,3R,4R,1'R,2'S,3'R,4'R)-3'-[3-(3,4-dimethoxy-phenyl)-3-oxo-propionyloxy]-4,7,7,4',7',7'-hexamethyl-[2,2']bi[bicyclo[2.2.1]heptyl]-3-yl ester

Base Information

• Chemical Name: 3-(3,4-Dimethoxy-phenyl)-3-oxo-propionic acid (1R,2S,3R,4R,1'R,2'S,3'R,4'R)-3'-[3-(3,4-dimethoxy-phenyl)-3-oxo-propionyloxy]-4,7,7,4',7',7'-hexamethyl-[2,2']bi[bicyclo[2.2.1]heptyl]-3-yl ester
• CAS No.: 620945-82-6
• Molecular Formula: C₄₂H₅₄O₁₀
• Molecular Weight: 718.885

Synonyms:

Chemical Property of 3-(3,4-Dimethoxy-phenyl)-3-oxo-propionic acid (1R,2S,3R,4R,1'R,2'S,3'R,4'R)-3'-[3-(3,4-dimethoxy-phenyl)-3-oxo-propionyloxy]-4,7,7,4',7',7'-hexamethyl-[2,2']bi[bicyclo[2.2.1]heptyl]-3-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-(3,4-Dimethoxy-phenyl)-3-oxo-propionic acid (1R,2S,3R,4R,1'R,2'S,3'R,4'R)-3'-[3-(3,4-dimethoxy-phenyl)-3-oxo-propionyloxy]-4,7,7,4',7',7'-hexamethyl-[2,2']bi[bicyclo[2.2.1]heptyl]-3-yl ester

There total 5 articles about 3-(3,4-Dimethoxy-phenyl)-3-oxo-propionic acid (1R,2S,3R,4R,1'R,2'S,3'R,4'R)-3'-[3-(3,4-dimethoxy-phenyl)-3-oxo-propionyloxy]-4,7,7,4',7',7'-hexamethyl-[2,2']bi[bicyclo[2.2.1]heptyl]-3-yl ester 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:

3-Benzo[1,3]dioxol-5-yl-3-hydroxy-propionic acid (1R,2S,3R,4R,1'R,2'S,3'R,4'R)-3'-(3-benzo[1,3]dioxol-5-yl-3-hydroxy-propionyloxy)-4,7,7,4',7',7'-hexamethyl-[2,2']bi[bicyclo[2.2.1]heptyl]-3-yl ester (620945-74-6) → 3-(3,4-Dimethoxy-phenyl)-3-oxo-propionic acid (1R,2S,3R,4R,1'R,2'S,3'R,4'R)-3'-[3-(3,4-dimethoxy-phenyl)-3-oxo-propionyloxy]-4,7,7,4',7',7'-hexamethyl-[2,2']bi[bicyclo[2.2.1]heptyl]-3-yl ester (620945-82-6)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 72 percent / Jones oxidation

2.1: NaH / dimethylformamide / 25 °C

2.2: Br₂ / dimethylformamide / 6 h / 25 °C

3.1: 90 percent / LAH / tetrahydrofuran / 6 h / Heating

4.1: 88 percent / NaH / dioxane

5.1: 87 percent / LDA / tetrahydrofuran

6.1: 77 percent / Jones oxidation

With lithium aluminium tetrahydride; sodium hydride; lithium diisopropyl amide; In tetrahydrofuran; 1,4-dioxane; N,N-dimethyl-formamide; 1.1: Jones oxidation / 6.1: Jones oxidation;

DOI:10.1016/S0957-4166(03)00572-X

Reference yield:

3-Benzo[1,3]dioxol-5-yl-3-oxo-propionic acid (1R,2S,3R,4R,1'R,2'S,3'R,4'R)-3'-(3-benzo[1,3]dioxol-5-yl-3-oxo-propionyloxy)-4,7,7,4',7',7'-hexamethyl-[2,2']bi[bicyclo[2.2.1]heptyl]-3-yl ester (620945-75-7) → 3-(3,4-Dimethoxy-phenyl)-3-oxo-propionic acid (1R,2S,3R,4R,1'R,2'S,3'R,4'R)-3'-[3-(3,4-dimethoxy-phenyl)-3-oxo-propionyloxy]-4,7,7,4',7',7'-hexamethyl-[2,2']bi[bicyclo[2.2.1]heptyl]-3-yl ester (620945-82-6)

Guidance literature:

Multi-step reaction with 5 steps

1.1: NaH / dimethylformamide / 25 °C

1.2: Br₂ / dimethylformamide / 6 h / 25 °C

2.1: 90 percent / LAH / tetrahydrofuran / 6 h / Heating

3.1: 88 percent / NaH / dioxane

4.1: 87 percent / LDA / tetrahydrofuran

5.1: 77 percent / Jones oxidation

With lithium aluminium tetrahydride; sodium hydride; lithium diisopropyl amide; In tetrahydrofuran; 1,4-dioxane; N,N-dimethyl-formamide; 5.1: Jones oxidation;

DOI:10.1016/S0957-4166(03)00572-X

Reference yield:

(1R,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one (464-49-3,68546-28-1) → 3-(3,4-Dimethoxy-phenyl)-3-oxo-propionic acid (1R,2S,3R,4R,1'R,2'S,3'R,4'R)-3'-[3-(3,4-dimethoxy-phenyl)-3-oxo-propionyloxy]-4,7,7,4',7',7'-hexamethyl-[2,2']bi[bicyclo[2.2.1]heptyl]-3-yl ester (620945-82-6)

Guidance literature:

Multi-step reaction with 4 steps

1.1: BuLi; PhI(OAc)2 / tetrahydrofuran

1.2: 54 percent / LAH / tetrahydrofuran

2.1: 88 percent / NaH / dioxane

3.1: 87 percent / LDA / tetrahydrofuran

4.1: 77 percent / Jones oxidation

With n-butyllithium; [bis(acetoxy)iodo]benzene; sodium hydride; lithium diisopropyl amide; In tetrahydrofuran; 1,4-dioxane; 4.1: Jones oxidation;

DOI:10.1016/S0957-4166(03)00572-X

upstream raw materials:

(1R,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one

(1R,1'R)-exo,exo'-3,3'-biisoborneol

Acetic acid (1R,2S,3R,4R,1'R,2'S,3'R,4'R)-3'-acetoxy-4,7,7,4',7',7'-hexamethyl-[2,2']bi[bicyclo[2.2.1]heptyl]-3-yl ester

3-Benzo[1,3]dioxol-5-yl-3-hydroxy-propionic acid (1R,2S,3R,4R,1'R,2'S,3'R,4'R)-3'-(3-benzo[1,3]dioxol-5-yl-3-hydroxy-propionyloxy)-4,7,7,4',7',7'-hexamethyl-[2,2']bi[bicyclo[2.2.1]heptyl]-3-yl ester

Downstream raw materials:

(2S,3S)-2,3-Bis<(3,4-dimethoxyphenyl)hydroxymethyl>-1,4-butanediol

eudesmine

C₄₂H₅₂O₁₀

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