[(S)-1-[3-(2-benzyloxyethyl)-2,5-dimethoxy-4-methyl-6-vinylphenyl]-2-methylallyloxy]-tert-butyldimethylsilane

Base Information

• Chemical Name: [(S)-1-[3-(2-benzyloxyethyl)-2,5-dimethoxy-4-methyl-6-vinylphenyl]-2-methylallyloxy]-tert-butyldimethylsilane
• CAS No.: 479633-96-0
• Molecular Formula: C₃₀H₄₄O₄Si
• Molecular Weight: 496.762

Synonyms:[(S)-1-[3-(2-benzyloxyethyl)-2,5-dimethoxy-4-methyl-6-vinylphenyl]-2-methylallyloxy]-tert-butyldimethylsilane

Chemical Property of [(S)-1-[3-(2-benzyloxyethyl)-2,5-dimethoxy-4-methyl-6-vinylphenyl]-2-methylallyloxy]-tert-butyldimethylsilane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of [(S)-1-[3-(2-benzyloxyethyl)-2,5-dimethoxy-4-methyl-6-vinylphenyl]-2-methylallyloxy]-tert-butyldimethylsilane

There total 21 articles about [(S)-1-[3-(2-benzyloxyethyl)-2,5-dimethoxy-4-methyl-6-vinylphenyl]-2-methylallyloxy]-tert-butyldimethylsilane 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:

2-bromo-6-hydroxy-4-methylbenzaldehyde (139976-21-9) → [(S)-1-[3-(2-benzyloxyethyl)-2,5-dimethoxy-4-methyl-6-vinylphenyl]-2-methylallyloxy]-tert-butyldimethylsilane (479633-96-0)

Guidance literature:

Multi-step reaction with 17 steps

1.1: 79 percent / sodium hydride / dimethylformamide / 7 h

2.1: 66 percent / decahydronaphthalene / 7 h / Heating

3.1: 83 percent / PhI(OAc)2

4.1: 70 percent / zinc; acetic acid / 7 h

5.1: 92 percent / K₂CO₃ / dimethylformamide

6.1: 97 percent / TsOH*H₂O / methanol / Heating

7.1: 95 percent / OsO₄; NaIO₄ / CCl₄; H₂O; 2-methyl-propan-2-ol / 1.5 h

8.1: 95 percent / NaBH₄ / methanol / 1.5 h / 0 °C

9.1: 92 percent / sodium hydride / tetrahydrofuran; various solvent(s) / 0 °C

10.1: 95 percent / Amberlite IR 120 / acetone; H₂O

11.1: 66 percent / Pd(PPh₃)4; CuI / toluene / 40 h / Heating

12.1: Bu₂BOSO₂CF₃; diisopropylethylamine / CH₂Cl₂ / 2 h / -78 - 0 °C

12.2: CH₂Cl₂ / 7.5 h

12.3: 87 percent / H₂O₂ / CH₂Cl₂; methanol; H₂O / 1 h / 0 °C / pH 7

13.1: 95 percent / 2,6-lutidine / CH₂Cl₂ / 1 h

14.1: 89 percent / n-BuLi / hexane; tetrahydrofuran / 6 h / 0 °C

15.1: 89 percent / iBu₂AlH / CH₂Cl₂ / -78 - 0 °C

16.1: 93 percent / n-Bu₃P / tetrahydrofuran

17.1: 22 mg / H₂O₂ / tetrahydrofuran / 5 h

With 2,6-dimethylpyridine; sodium tetrahydroborate; sodium periodate; copper(l) iodide; osmium(VIII) oxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; tributylphosphine; [bis(acetoxy)iodo]benzene; Amberlite IR 120; di-n-butylboryl trifluoromethanesulfonate; dihydrogen peroxide; sodium hydride; diisobutylaluminium hydride; potassium carbonate; toluene-4-sulfonic acid; acetic acid; N-ethyl-N,N-diisopropylamine; zinc; In tetrahydrofuran; methanol; tetrachloromethane; hexane; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; decalin; tert-butyl alcohol; 2.1: Claisen rearrangement / 11.1: Stille coupling;

DOI:10.1021/jo040115b

Reference yield:

2-allyloxy-6-bromo-4-methylbenzaldehyde (479633-77-7) → [(S)-1-[3-(2-benzyloxyethyl)-2,5-dimethoxy-4-methyl-6-vinylphenyl]-2-methylallyloxy]-tert-butyldimethylsilane (479633-96-0)

Guidance literature:

Multi-step reaction with 16 steps

1.1: 66 percent / decahydronaphthalene / 7 h / Heating

2.1: 83 percent / PhI(OAc)2

3.1: 70 percent / zinc; acetic acid / 7 h

4.1: 92 percent / K₂CO₃ / dimethylformamide

5.1: 97 percent / TsOH*H₂O / methanol / Heating

6.1: 95 percent / OsO₄; NaIO₄ / CCl₄; H₂O; 2-methyl-propan-2-ol / 1.5 h

7.1: 95 percent / NaBH₄ / methanol / 1.5 h / 0 °C

8.1: 92 percent / sodium hydride / tetrahydrofuran; various solvent(s) / 0 °C

9.1: 95 percent / Amberlite IR 120 / acetone; H₂O

10.1: 66 percent / Pd(PPh₃)4; CuI / toluene / 40 h / Heating

11.1: Bu₂BOSO₂CF₃; diisopropylethylamine / CH₂Cl₂ / 2 h / -78 - 0 °C

11.2: CH₂Cl₂ / 7.5 h

11.3: 87 percent / H₂O₂ / CH₂Cl₂; methanol; H₂O / 1 h / 0 °C / pH 7

12.1: 95 percent / 2,6-lutidine / CH₂Cl₂ / 1 h

13.1: 89 percent / n-BuLi / hexane; tetrahydrofuran / 6 h / 0 °C

14.1: 89 percent / iBu₂AlH / CH₂Cl₂ / -78 - 0 °C

15.1: 93 percent / n-Bu₃P / tetrahydrofuran

16.1: 22 mg / H₂O₂ / tetrahydrofuran / 5 h

With 2,6-dimethylpyridine; sodium tetrahydroborate; sodium periodate; copper(l) iodide; osmium(VIII) oxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; tributylphosphine; [bis(acetoxy)iodo]benzene; Amberlite IR 120; di-n-butylboryl trifluoromethanesulfonate; dihydrogen peroxide; sodium hydride; diisobutylaluminium hydride; potassium carbonate; toluene-4-sulfonic acid; acetic acid; N-ethyl-N,N-diisopropylamine; zinc; In tetrahydrofuran; methanol; tetrachloromethane; hexane; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; decalin; tert-butyl alcohol; 1.1: Claisen rearrangement / 10.1: Stille coupling;

DOI:10.1021/jo040115b

Reference yield:

3-allyl-6-bromo-2-hydroxy-5-methoxy-4-methylbenzaldehyde (479633-80-2) → [(S)-1-[3-(2-benzyloxyethyl)-2,5-dimethoxy-4-methyl-6-vinylphenyl]-2-methylallyloxy]-tert-butyldimethylsilane (479633-96-0)

Guidance literature:

Multi-step reaction with 13 steps

1.1: 92 percent / K₂CO₃ / dimethylformamide

2.1: 97 percent / TsOH*H₂O / methanol / Heating

3.1: 95 percent / OsO₄; NaIO₄ / CCl₄; H₂O; 2-methyl-propan-2-ol / 1.5 h

4.1: 95 percent / NaBH₄ / methanol / 1.5 h / 0 °C

5.1: 92 percent / sodium hydride / tetrahydrofuran; various solvent(s) / 0 °C

6.1: 95 percent / Amberlite IR 120 / acetone; H₂O

7.1: 66 percent / Pd(PPh₃)4; CuI / toluene / 40 h / Heating

8.1: Bu₂BOSO₂CF₃; diisopropylethylamine / CH₂Cl₂ / 2 h / -78 - 0 °C

8.2: CH₂Cl₂ / 7.5 h

8.3: 87 percent / H₂O₂ / CH₂Cl₂; methanol; H₂O / 1 h / 0 °C / pH 7

9.1: 95 percent / 2,6-lutidine / CH₂Cl₂ / 1 h

10.1: 89 percent / n-BuLi / hexane; tetrahydrofuran / 6 h / 0 °C

11.1: 89 percent / iBu₂AlH / CH₂Cl₂ / -78 - 0 °C

12.1: 93 percent / n-Bu₃P / tetrahydrofuran

13.1: 22 mg / H₂O₂ / tetrahydrofuran / 5 h

With 2,6-dimethylpyridine; sodium tetrahydroborate; sodium periodate; copper(l) iodide; osmium(VIII) oxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; tributylphosphine; Amberlite IR 120; di-n-butylboryl trifluoromethanesulfonate; dihydrogen peroxide; sodium hydride; diisobutylaluminium hydride; potassium carbonate; toluene-4-sulfonic acid; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; tetrachloromethane; hexane; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; tert-butyl alcohol; 7.1: Stille coupling;

DOI:10.1021/jo040115b

upstream raw materials:

2-bromo-6-hydroxy-4-methylbenzaldehyde

2-allyloxy-6-bromo-4-methylbenzaldehyde

3-allyl-6-bromo-2-hydroxy-4-methylbenzaldehyde

3-allyl-6-bromo-2-hydroxy-5-methoxy-4-methylbenzaldehyde

Downstream raw materials:

(S)-1-[3-(2-benzyloxyethyl)-2,5-dimethoxy-4-methyl-6-vinylphenyl]-2-methylprop-2-en-1-ol

(S)-6-(2-benzyloxyethyl)-4,7-dimethoxy-2,5-dimethyl-1H-inden-1-ol

(3aR,8bS)-7-(2-benzyloxyethyl)-5,8-dimethoxy-3a,6-dimethyl-4,8b-dihydro-3aH-indeno[1,2-b]furan

(S)-5-(2-benzyloxyethyl)-4,7-dimethoxy-2,6-dimethylindan-2-carboxylic acid methyl ester

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