2-Butanone, 3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-4-[4-[[(1,1-dimethylethyl)dimethyl silyl]oxy]phenyl]-1-phenyl-, (3S)-

Base Information

• Chemical Name: 2-Butanone, 3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-4-[4-[[(1,1-dimethylethyl)dimethyl silyl]oxy]phenyl]-1-phenyl-, (3S)-
• CAS No.: 193696-36-5
• Molecular Formula: C28H44O3Si2
• Molecular Weight: 484.827
• Mol file: 193696-36-5.mol

Synonyms:

Chemical Property of 2-Butanone, 3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-4-[4-[[(1,1-dimethylethyl)dimethyl silyl]oxy]phenyl]-1-phenyl-, (3S)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-Butanone, 3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-4-[4-[[(1,1-dimethylethyl)dimethyl silyl]oxy]phenyl]-1-phenyl-, (3S)-

There total 7 articles about 2-Butanone, 3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-4-[4-[[(1,1-dimethylethyl)dimethyl silyl]oxy]phenyl]-1-phenyl-, (3S)- 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%

(2S,3R)-2,4'-di-t-butyldimethylsiloxy-3-hydroxy-1,4-diphenylbutane (193696-34-3) → (2S)-2,4'-di-t-butyldimethylsiloxy-1,4-diphenyl-3-butanone (193696-36-5)

Guidance literature:

With pyridine; dicyclohexyl-carbodiimide; trifluoroacetic anhydride; In dimethyl sulfoxide; benzene;

DOI:10.7164/antibiotics.50.453

Reference yield:

p-hydroxyphenethyl alcohol (501-94-0) → (2S)-2,4'-di-t-butyldimethylsiloxy-1,4-diphenyl-3-butanone (193696-36-5)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 71 percent / Et₃N; SO₃-pyridine / dimethylsulfoxide / 1 h

2.1: 63 percent / tetrahydrofuran / 0.42 h / -76 °C

3.1: 4 Angstroem molecular sieves; tetraisopropyl orthotitanate; (+)-diisopropyl-L-tartrate / CH₂Cl₂ / 0.5 h / -5 °C

3.2: 35 percent / cumene hydroperoxide / CH₂Cl₂ / 48 h / -20 °C

4.1: 71 percent / imidazole / dimethylformamide / 3 h / 20 °C

5.1: 75 percent / CuI / tetrahydrofuran / 0.58 h / -40 °C

6.1: 88 percent / DCC; DMSO; TFA / pyridine; benzene / 3 h / 20 °C

With 1H-imidazole; titanium(IV) isopropylate; copper(l) iodide; pyridine-SO₃ complex; L-(+)-diisopropyl tartrate; 4 A molecular sieve; dimethyl sulfoxide; triethylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; In tetrahydrofuran; pyridine; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; benzene; 1.1: Oxidation / 2.1: Grignard reaction / 3.1: asymmetric epoxidation / 3.2: Oxidation / 4.1: Substitution / 5.1: Grignard reaction / 6.1: Oxidation;

Reference yield:

4-hydroxyphenylacetaldehyde (7339-87-9) → (2S)-2,4'-di-t-butyldimethylsiloxy-1,4-diphenyl-3-butanone (193696-36-5)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 63 percent / tetrahydrofuran / 0.42 h / -76 °C

2.1: 4 Angstroem molecular sieves; tetraisopropyl orthotitanate; (+)-diisopropyl-L-tartrate / CH₂Cl₂ / 0.5 h / -5 °C

2.2: 35 percent / cumene hydroperoxide / CH₂Cl₂ / 48 h / -20 °C

3.1: 71 percent / imidazole / dimethylformamide / 3 h / 20 °C

4.1: 75 percent / CuI / tetrahydrofuran / 0.58 h / -40 °C

5.1: 88 percent / DCC; DMSO; TFA / pyridine; benzene / 3 h / 20 °C

With 1H-imidazole; titanium(IV) isopropylate; copper(l) iodide; L-(+)-diisopropyl tartrate; 4 A molecular sieve; dimethyl sulfoxide; dicyclohexyl-carbodiimide; trifluoroacetic acid; In tetrahydrofuran; pyridine; dichloromethane; N,N-dimethyl-formamide; benzene; 1.1: Grignard reaction / 2.1: asymmetric epoxidation / 2.2: Oxidation / 3.1: Substitution / 4.1: Grignard reaction / 5.1: Oxidation;

upstream raw materials:

(2S,3R)-2,4'-di-t-butyldimethylsiloxy-3-hydroxy-1,4-diphenylbutane

p-hydroxyphenethyl alcohol

4-hydroxyphenylacetaldehyde

(2S,3R)-3,4-epoxy-2-hydroxy-1-(4'-hydroxyphenyl)butane