(R)-1-(4-(tert-butyldimethylsilyloxy)-3-methoxyphenyl)ethane-1,2-diol

Base Information

• Chemical Name: (R)-1-(4-(tert-butyldimethylsilyloxy)-3-methoxyphenyl)ethane-1,2-diol
• CAS No.: 1435896-50-6
• Molecular Formula: C₁₅H₂₆O₄Si
• Molecular Weight: 298.455
• Mol file: 1435896-50-6.mol

Synonyms:(R)-1-(4-(tert-butyldimethylsilyloxy)-3-methoxyphenyl)ethane-1,2-diol

Chemical Property of (R)-1-(4-(tert-butyldimethylsilyloxy)-3-methoxyphenyl)ethane-1,2-diol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-1-(4-(tert-butyldimethylsilyloxy)-3-methoxyphenyl)ethane-1,2-diol

There total 3 articles about (R)-1-(4-(tert-butyldimethylsilyloxy)-3-methoxyphenyl)ethane-1,2-diol 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: 88.0%

(1,1-dimethylethyl)(4-ethenyl-2-methoxyphenoxy)dimethylsilane (828269-23-4) → (R)-1-(4-(tert-butyldimethylsilyloxy)-3-methoxyphenyl)ethane-1,2-diol (1435896-50-6)

Guidance literature:

With AD-mix-α; In water; tert-butyl alcohol; at 0 - 25 ℃; for 1.66667h; enantioselective reaction; Inert atmosphere;

DOI:10.1002/chir.22108

Reference yield:

vanillin (121-33-5,8014-42-4) → (R)-1-(4-(tert-butyldimethylsilyloxy)-3-methoxyphenyl)ethane-1,2-diol (1435896-50-6)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 1H-imidazole / N,N-dimethyl-formamide / 12 h / 0 - 25 °C / Inert atmosphere

2.1: potassium tert-butylate / tetrahydrofuran / 0.17 h / Inert atmosphere

2.2: 12 h / -78 - 25 °C / Inert atmosphere

3.1: AD-mix-α / tert-butyl alcohol; water / 1.67 h / 0 - 25 °C / Inert atmosphere

With 1H-imidazole; AD-mix-α; potassium tert-butylate; In tetrahydrofuran; water; N,N-dimethyl-formamide; tert-butyl alcohol; 2.1: |Wittig Olefination / 2.2: |Wittig Olefination / 3.1: |Sharpless Dihydroxylation;

DOI:10.1002/chir.22108

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → (R)-1-(4-(tert-butyldimethylsilyloxy)-3-methoxyphenyl)ethane-1,2-diol (1435896-50-6)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 1H-imidazole / N,N-dimethyl-formamide / 12 h / 0 - 25 °C / Inert atmosphere

2.1: potassium tert-butylate / tetrahydrofuran / 0.17 h / Inert atmosphere

2.2: 12 h / -78 - 25 °C / Inert atmosphere

3.1: AD-mix-α / tert-butyl alcohol; water / 1.67 h / 0 - 25 °C / Inert atmosphere

With 1H-imidazole; AD-mix-α; potassium tert-butylate; In tetrahydrofuran; water; N,N-dimethyl-formamide; tert-butyl alcohol; 2.1: |Wittig Olefination / 2.2: |Wittig Olefination / 3.1: |Sharpless Dihydroxylation;

DOI:10.1002/chir.22108

upstream raw materials:

vanillin

tert-butyldimethylsilyl chloride

(1,1-dimethylethyl)(4-ethenyl-2-methoxyphenoxy)dimethylsilane

Downstream raw materials:

(R)-2-(4-(tert-butyldimethylsilyloxy)-3-methoxyphenyl)-2-hydroxyethyl 4-methylbenzenesulfonate

(R)-normetanephrine