rac-1-{4-[(1,1-dimethylethyl)diphenylsilyloxymethyl]-2,6-dimethoxyphenyl}pent-1-en-3-ol

Base Information

• Chemical Name: rac-1-{4-[(1,1-dimethylethyl)diphenylsilyloxymethyl]-2,6-dimethoxyphenyl}pent-1-en-3-ol
• CAS No.: 276880-07-0
• Molecular Formula: C₃₀H₃₈O₄Si
• Molecular Weight: 490.715
• Mol file: 276880-07-0.mol

Synonyms:rac-1-{4-[(1,1-dimethylethyl)diphenylsilyloxymethyl]-2,6-dimethoxyphenyl}pent-1-en-3-ol

Chemical Property of rac-1-{4-[(1,1-dimethylethyl)diphenylsilyloxymethyl]-2,6-dimethoxyphenyl}pent-1-en-3-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of rac-1-{4-[(1,1-dimethylethyl)diphenylsilyloxymethyl]-2,6-dimethoxyphenyl}pent-1-en-3-ol

There total 5 articles about rac-1-{4-[(1,1-dimethylethyl)diphenylsilyloxymethyl]-2,6-dimethoxyphenyl}pent-1-en-3-ol 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: 97.0%

1-{4-[(1,1-dimethylethyl)diphenylsilyloxymethyl]-2,6-dimethoxyphenyl}pent-1-en-3-one (276880-06-9) → rac-1-{4-[(1,1-dimethylethyl)diphenylsilyloxymethyl]-2,6-dimethoxyphenyl}pent-1-en-3-ol (276880-07-0)

Guidance literature:

With sodium tetrahydroborate; cerium(III) chloride; In ethanol; at 0 ℃;

DOI:10.1021/ja000429q

Reference yield:

(4-bromo-3,5-dimethoxyphenyl)methanol (61367-62-2) → rac-1-{4-[(1,1-dimethylethyl)diphenylsilyloxymethyl]-2,6-dimethoxyphenyl}pent-1-en-3-ol (276880-07-0)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 98 percent / Et₃N; DMAP / CH₂Cl₂ / -20 - 20 °C

2.1: t-BuLi / ethanol; pentane / 0.5 h / -78 °C

2.2: 92 percent / ethanol; pentane / -78 - 20 °C

3.1: 70 percent / DBU; lithium chloride / acetonitrile / 36 h

4.1: 97 percent / NaBH₄; CeCl₃*7H₂O / ethanol / 0 °C

With dmap; sodium tetrahydroborate; cerium(III) chloride; tert.-butyl lithium; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; lithium chloride; In ethanol; dichloromethane; acetonitrile; pentane; 1.1: sililation / 2.1: Metallation / 2.2: Formylation / 3.1: Masamune olefination / 4.1: Reduction;

DOI:10.1021/ja000429q

Reference yield:

tert-butylchlorodiphenylsilane (58479-61-1) → rac-1-{4-[(1,1-dimethylethyl)diphenylsilyloxymethyl]-2,6-dimethoxyphenyl}pent-1-en-3-ol (276880-07-0)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 98 percent / Et₃N; DMAP / CH₂Cl₂ / -20 - 20 °C

2.1: t-BuLi / ethanol; pentane / 0.5 h / -78 °C

2.2: 92 percent / ethanol; pentane / -78 - 20 °C

3.1: 70 percent / DBU; lithium chloride / acetonitrile / 36 h

4.1: 97 percent / NaBH₄; CeCl₃*7H₂O / ethanol / 0 °C

With dmap; sodium tetrahydroborate; cerium(III) chloride; tert.-butyl lithium; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; lithium chloride; In ethanol; dichloromethane; acetonitrile; pentane; 1.1: sililation / 2.1: Metallation / 2.2: Formylation / 3.1: Masamune olefination / 4.1: Reduction;

DOI:10.1021/ja000429q

upstream raw materials:

1-{4-[(1,1-dimethylethyl)diphenylsilyloxymethyl]-2,6-dimethoxyphenyl}pent-1-en-3-one

(4-bromo-3,5-dimethoxyphenyl)methanol

tert-butylchlorodiphenylsilane

2,6-dimethoxy-4-[(1,1-dimethylethyl)diphenylsilyloxymethyl]benzaldehyde

Downstream raw materials:

(+)-(R)-1-{4-[(1,1-dimethylethyl)diphenylsilyloxymethyl]-2,6-dimethoxyphenyl}pent-1-en-3-ol, 3-acetate

(7S)-methyl 2-(dimethoxyphosphoryl)-7-(4-formyl-2,6-dimethoxyphenyl)undecanoate

(4E,7S)-methyl 2-(dimethoxyphosphoryl)-7-(4-formyl-2,6-dimethoxyphenyl)undec-4-enoate

(7S)-methyl 2-(dimethoxyphosphoryl)-7-(4-hydroxymethyl-2,6-dimethoxyphenyl)undecanoate