3-[3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-phenyl]-propionic acid (1R,3S)-3-(4-methoxy-benzyloxy)-1-methyl-hex-5-enyl ester

Base Information

• Chemical Name: 3-[3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-phenyl]-propionic acid (1R,3S)-3-(4-methoxy-benzyloxy)-1-methyl-hex-5-enyl ester
• CAS No.: 866455-75-6
• Molecular Formula: C₃₆H₅₈O₆Si₂
• Molecular Weight: 643.024
• Mol file: 866455-75-6.mol

Synonyms:3-[3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-phenyl]-propionic acid (1R,3S)-3-(4-methoxy-benzyloxy)-1-methyl-hex-5-enyl ester

Chemical Property of 3-[3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-phenyl]-propionic acid (1R,3S)-3-(4-methoxy-benzyloxy)-1-methyl-hex-5-enyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-[3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-phenyl]-propionic acid (1R,3S)-3-(4-methoxy-benzyloxy)-1-methyl-hex-5-enyl ester

There total 5 articles about 3-[3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-phenyl]-propionic acid (1R,3S)-3-(4-methoxy-benzyloxy)-1-methyl-hex-5-enyl 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: 86.0%

(2R,4S)-4-(4-Methoxy-benzyloxy)-hept-6-en-2-ol (866455-60-9) + 3,4-bis(O-tert-butyldimethylsilyl)-3,4-dihydroxyhydrocinnamic acid (116511-71-8) → 3-[3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-phenyl]-propionic acid (1R,3S)-3-(4-methoxy-benzyloxy)-1-methyl-hex-5-enyl ester (866455-75-6)

Guidance literature:

With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 0 - 20 ℃; for 2h;

DOI:10.1016/j.tetlet.2005.07.075

Reference yield:

(S)-1-(1,4-Dioxa-spiro[4.5]dec-2-yl)-pent-4-en-2-one (866455-67-6) → 3-[3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-phenyl]-propionic acid (1R,3S)-3-(4-methoxy-benzyloxy)-1-methyl-hex-5-enyl ester (866455-75-6)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 94 percent / LiAlH₄; LiI / diethyl ether; tetrahydrofuran / -100 °C

2.1: 87 percent / NaH / tetrahydrofuran

3.1: 90 percent / PTSA / aq. methanol / 0.5 h / 0 °C

4.1: Et₃N / DMAP / CH₂Cl₂ / 3 h

4.2: 72 percent / LiAlH₄ / tetrahydrofuran / 3 h / 20 °C

5.1: 86 percent / DCC; DMAP / CH₂Cl₂ / 2 h / 0 - 20 °C

With dmap; lithium aluminium tetrahydride; sodium hydride; toluene-4-sulfonic acid; triethylamine; dicyclohexyl-carbodiimide; lithium iodide; dmap; In tetrahydrofuran; methanol; diethyl ether; dichloromethane;

DOI:10.1016/j.tetlet.2005.07.075

Reference yield:

1-[(2S)-1,4-dioxaspiro[4,5]dec-2-yl]-4-penten-2-ol (866455-65-4) → 3-[3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-phenyl]-propionic acid (1R,3S)-3-(4-methoxy-benzyloxy)-1-methyl-hex-5-enyl ester (866455-75-6)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 85 percent / IBX / dimethylsulfoxide; CH₂Cl₂ / 3 h

2.1: 94 percent / LiAlH₄; LiI / diethyl ether; tetrahydrofuran / -100 °C

3.1: 87 percent / NaH / tetrahydrofuran

4.1: 90 percent / PTSA / aq. methanol / 0.5 h / 0 °C

5.1: Et₃N / DMAP / CH₂Cl₂ / 3 h

5.2: 72 percent / LiAlH₄ / tetrahydrofuran / 3 h / 20 °C

6.1: 86 percent / DCC; DMAP / CH₂Cl₂ / 2 h / 0 - 20 °C

With dmap; lithium aluminium tetrahydride; sodium hydride; toluene-4-sulfonic acid; triethylamine; dicyclohexyl-carbodiimide; lithium iodide; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; dmap; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; dimethyl sulfoxide;

DOI:10.1016/j.tetlet.2005.07.075

upstream raw materials:

(2R,4S)-4-(4-Methoxy-benzyloxy)-hept-6-en-2-ol

3,4-bis(O-tert-butyldimethylsilyl)-3,4-dihydroxyhydrocinnamic acid

(S)-1-(1,4-Dioxa-spiro[4.5]dec-2-yl)-pent-4-en-2-one

1-[(2S)-1,4-dioxaspiro[4,5]dec-2-yl]-4-penten-2-ol

Downstream raw materials:

Acrylic acid (S)-1-((R)-2-{3-[3,4-bis-(tert-butyl-dimethyl-silanyloxy)-phenyl]-propionyloxy}-propyl)-but-3-enyl ester

(-)-<5(S),7(R)>-7-<5-(oct-2-enolide)-3',4'-bis-(t-butyldimethylsilyloxy)>-dihydrocinnamate

(R)-1-methyl-2-[(S)-6-oxo-3,6-dihydro-2H-pyran-2-yl]ethyl 3-(3,4-dihydroxyphenyl)propanoate

3-[3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-phenyl]-propionic acid (1R,3S)-3-hydroxy-1-methyl-hex-5-enyl ester