3-(S)-t-butyldimethylsilyloxy-4-(3-methoxymethylphenyl)-1-butyne

Base Information

• Chemical Name: 3-(S)-t-butyldimethylsilyloxy-4-(3-methoxymethylphenyl)-1-butyne
• CAS No.: 253350-39-9
• Molecular Formula: C₁₈H₂₈O₂Si
• Molecular Weight: 304.505
• Mol file: 253350-39-9.mol

Synonyms:3-(S)-t-butyldimethylsilyloxy-4-(3-methoxymethylphenyl)-1-butyne

Chemical Property of 3-(S)-t-butyldimethylsilyloxy-4-(3-methoxymethylphenyl)-1-butyne

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-(S)-t-butyldimethylsilyloxy-4-(3-methoxymethylphenyl)-1-butyne

There total 9 articles about 3-(S)-t-butyldimethylsilyloxy-4-(3-methoxymethylphenyl)-1-butyne 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%

tert-butyldimethylsilyl chloride (18162-48-6) + (3S)-4-(3-methoxymethylphenyl)-1-butyn-3-ol (253350-38-8) → 3-(S)-t-butyldimethylsilyloxy-4-(3-methoxymethylphenyl)-1-butyne (253350-39-9)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; at 20 ℃;

DOI:10.1016/S0968-0896(02)00031-7

Reference yield:

3-(methoxymethyl)bromobenzene (1515-89-5) → 3-(S)-t-butyldimethylsilyloxy-4-(3-methoxymethylphenyl)-1-butyne (253350-39-9)

Guidance literature:

Multi-step reaction with 10 steps

1.1: Mg; CuI / tetrahydrofuran / 0.5 h / 0 °C

1.2: 95.8 g / tetrahydrofuran / 0.33 h

2.1: 46.9 g / AcOH; H₂O / tetrahydrofuran / 3 h / 65 °C

3.1: 2,4,6-collidine / CH₂Cl₂ / 0.33 h / -78 °C

4.1: 57.6 g / p-TsOH*H₂O / CH₂Cl₂ / 0.5 h / 20 °C

5.1: 92 percent / 2N NaOH / methanol / 0.5 h / 20 °C

6.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -70 - -30 °C

7.1: 49.2 g / PPh₃; Et₃N / CH₂Cl₂ / 0.25 h / -40 °C

8.1: n-BuLi / tetrahydrofuran; hexane / 0.25 h / -70 °C

9.1: 58 percent / p-TsOH*H₂O / methanol / 0.5 h / 20 °C

10.1: 97 percent / imidazole / dimethylformamide / 20 °C

With 1H-imidazole; 2,4,6-trimethyl-pyridine; sodium hydroxide; copper(l) iodide; n-butyllithium; oxalyl dichloride; water; toluene-4-sulfonic acid; magnesium; acetic acid; dimethyl sulfoxide; triethylamine; triphenylphosphine; In tetrahydrofuran; methanol; hexane; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0968-0896(02)00031-7

Reference yield:

(2S)-3-(3-methoxymethylphenyl)propan-1,2-diol (253350-31-1) → 3-(S)-t-butyldimethylsilyloxy-4-(3-methoxymethylphenyl)-1-butyne (253350-39-9)

Guidance literature:

Multi-step reaction with 8 steps

1: 2,4,6-collidine / CH₂Cl₂ / 0.33 h / -78 °C

2: 57.6 g / p-TsOH*H₂O / CH₂Cl₂ / 0.5 h / 20 °C

3: 92 percent / 2N NaOH / methanol / 0.5 h / 20 °C

4: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -70 - -30 °C

5: 49.2 g / PPh₃; Et₃N / CH₂Cl₂ / 0.25 h / -40 °C

6: n-BuLi / tetrahydrofuran; hexane / 0.25 h / -70 °C

7: 58 percent / p-TsOH*H₂O / methanol / 0.5 h / 20 °C

8: 97 percent / imidazole / dimethylformamide / 20 °C

With 1H-imidazole; 2,4,6-trimethyl-pyridine; sodium hydroxide; n-butyllithium; oxalyl dichloride; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; triphenylphosphine; In tetrahydrofuran; methanol; hexane; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0968-0896(02)00031-7

upstream raw materials:

tert-butyldimethylsilyl chloride

(3S)-4-(3-methoxymethylphenyl)-1-butyn-3-ol

3-(methoxymethyl)bromobenzene

(2S)-3-(3-methoxymethylphenyl)propan-1,2-diol

Downstream raw materials:

7-[(1R,2R,3R,5S)-3-(tert-Butyl-dimethyl-silanyloxy)-2-[(E)-(S)-3-(tert-butyl-dimethyl-silanyloxy)-4-(3-methoxymethyl-phenyl)-but-1-enyl]-5-(toluene-4-sulfonyloxy)-cyclopentyl]-heptanoic acid methyl ester

7-{(1R,2R,3R,5S)-3-(tert-Butyl-dimethyl-silanyloxy)-2-[(E)-(S)-3-(tert-butyl-dimethyl-silanyloxy)-4-(3-methoxymethyl-phenyl)-but-1-enyl]-5-hydroxy-cyclopentyl}-heptanoic acid methyl ester

7-{(1R,2R,3R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-[(E)-(S)-3-(tert-butyl-dimethyl-silanyloxy)-4-(3-methoxymethyl-phenyl)-but-1-enyl]-5-oxo-cyclopentyl}-heptanoic acid methyl ester

(Z)-7-{(1R,2R,3R,5S)-3-(tert-Butyl-dimethyl-silanyloxy)-2-[(E)-(S)-3-(tert-butyl-dimethyl-silanyloxy)-4-(3-methoxymethyl-phenyl)-but-1-enyl]-5-hydroxy-cyclopentyl}-hept-5-enoic acid methyl ester