(2S,3S)-3-(p-methoxyphenyl)dimethylsilyl-1,2-heptanediol

Base Information

• Chemical Name: (2S,3S)-3-(p-methoxyphenyl)dimethylsilyl-1,2-heptanediol
• CAS No.: 252952-56-0
• Molecular Formula: C₁₆H₂₈O₃Si
• Molecular Weight: 296.482
• Mol file: 252952-56-0.mol

Synonyms:(2S,3S)-3-(p-methoxyphenyl)dimethylsilyl-1,2-heptanediol

Chemical Property of (2S,3S)-3-(p-methoxyphenyl)dimethylsilyl-1,2-heptanediol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S)-3-(p-methoxyphenyl)dimethylsilyl-1,2-heptanediol

There total 6 articles about (2S,3S)-3-(p-methoxyphenyl)dimethylsilyl-1,2-heptanediol 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: 90.0%

n-butyllithium (109-72-8,29786-93-4) + (2S,3S)-(p-methoxyphenyl)dimethylsilyl-2,3-epoxy-1-propanol (252952-48-0) → (2S,3S)-3-(p-methoxyphenyl)dimethylsilyl-1,2-heptanediol (252952-56-0)

Guidance literature:

With CuCN; In hexane; at -40 - -20 ℃; for 2h;

DOI:10.1016/S0957-4166(99)00383-3

Reference yield:

1-bromo-4-methoxy-benzene (104-92-7) → (2S,3S)-3-(p-methoxyphenyl)dimethylsilyl-1,2-heptanediol (252952-56-0)

Guidance literature:

Multi-step reaction with 6 steps

1.1: t-BuLi / pentane / 0.5 h / -78 - 0 °C

1.2: pentane / 2 h / -78 °C

2.1: n-BuLi / tetrahydrofuran / 0.5 h / -40 °C

2.2: tetrahydrofuran / 20 °C

3.1: PPTS; ethanol / 7 h / 55 °C

4.1: 94 percent / REDAL / toluene; diethyl ether / 3 h / 0 - 20 °C

5.1: 89 percent / t-butylhydroperoxide; (+)-diethyl tartrate; titanium tetraisopropoxide / CH₂Cl₂; 2,2,4-trimethyl-pentane / 5 h / -20 °C

6.1: 90 percent / CuCN / hexane / 2 h / -40 - -20 °C

With titanium(IV) isopropylate; tert.-butylhydroperoxide; n-butyllithium; ethanol; tert.-butyl lithium; pyridinium p-toluenesulfonate; (+)-Weinsaeure-diethylester; sodium bis(2-methoxyethoxy)aluminium dihydride; In tetrahydrofuran; 2,2,4-trimethylpentane; diethyl ether; hexane; dichloromethane; toluene; pentane; 1.1: Metallation / 1.2: Substitution / 2.1: Metallation / 2.2: Substitution / 3.1: deacetalization / 4.1: Reduction / 5.1: Epoxidation / 6.1: ring cleavage;

DOI:10.1016/S0957-4166(99)00383-3

Reference yield:

chlorodimethyl(4-methoxyphenyl)silane (2372-33-0) → (2S,3S)-3-(p-methoxyphenyl)dimethylsilyl-1,2-heptanediol (252952-56-0)

Guidance literature:

Multi-step reaction with 5 steps

1.1: n-BuLi / tetrahydrofuran / 0.5 h / -40 °C

1.2: tetrahydrofuran / 20 °C

2.1: PPTS; ethanol / 7 h / 55 °C

3.1: 94 percent / REDAL / toluene; diethyl ether / 3 h / 0 - 20 °C

4.1: 89 percent / t-butylhydroperoxide; (+)-diethyl tartrate; titanium tetraisopropoxide / CH₂Cl₂; 2,2,4-trimethyl-pentane / 5 h / -20 °C

5.1: 90 percent / CuCN / hexane / 2 h / -40 - -20 °C

With titanium(IV) isopropylate; tert.-butylhydroperoxide; n-butyllithium; ethanol; pyridinium p-toluenesulfonate; (+)-Weinsaeure-diethylester; sodium bis(2-methoxyethoxy)aluminium dihydride; In tetrahydrofuran; 2,2,4-trimethylpentane; diethyl ether; hexane; dichloromethane; toluene; 1.1: Metallation / 1.2: Substitution / 2.1: deacetalization / 3.1: Reduction / 4.1: Epoxidation / 5.1: ring cleavage;

DOI:10.1016/S0957-4166(99)00383-3

upstream raw materials:

n-butyllithium

(2S,3S)-(p-methoxyphenyl)dimethylsilyl-2,3-epoxy-1-propanol

1-bromo-4-methoxy-benzene

chlorodimethyl(4-methoxyphenyl)silane