(S)-4-(tert-Butyl-dimethyl-silanyloxy)-2-{3-(tert-butyl-dimethyl-silanyloxy)-3-[2-(3-hydroxy-prop-1-ynyl)-phenyl]-prop-1-ynyl}-cyclohex-2-enone

Base Information

• Chemical Name: (S)-4-(tert-Butyl-dimethyl-silanyloxy)-2-{3-(tert-butyl-dimethyl-silanyloxy)-3-[2-(3-hydroxy-prop-1-ynyl)-phenyl]-prop-1-ynyl}-cyclohex-2-enone
• CAS No.: 198407-85-1
• Molecular Formula: C₃₀H₄₄O₄Si₂
• Molecular Weight: 524.848
• Mol file: 198407-85-1.mol

Synonyms:(S)-4-(tert-Butyl-dimethyl-silanyloxy)-2-{3-(tert-butyl-dimethyl-silanyloxy)-3-[2-(3-hydroxy-prop-1-ynyl)-phenyl]-prop-1-ynyl}-cyclohex-2-enone

Chemical Property of (S)-4-(tert-Butyl-dimethyl-silanyloxy)-2-{3-(tert-butyl-dimethyl-silanyloxy)-3-[2-(3-hydroxy-prop-1-ynyl)-phenyl]-prop-1-ynyl}-cyclohex-2-enone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-4-(tert-Butyl-dimethyl-silanyloxy)-2-{3-(tert-butyl-dimethyl-silanyloxy)-3-[2-(3-hydroxy-prop-1-ynyl)-phenyl]-prop-1-ynyl}-cyclohex-2-enone

There total 8 articles about (S)-4-(tert-Butyl-dimethyl-silanyloxy)-2-{3-(tert-butyl-dimethyl-silanyloxy)-3-[2-(3-hydroxy-prop-1-ynyl)-phenyl]-prop-1-ynyl}-cyclohex-2-enone 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: 74.0%

(4S)-4-[(tert-Butyldimethylsilyl)oxy]-2-iodocyclohex-2-en-1-one (198407-83-9) + 3-{2-[1-(tert-Butyl-dimethyl-silanyloxy)-prop-2-ynyl]-phenyl}-prop-2-yn-1-ol (198407-80-6) → (S)-4-(tert-Butyl-dimethyl-silanyloxy)-2-{3-(tert-butyl-dimethyl-silanyloxy)-3-[2-(3-hydroxy-prop-1-ynyl)-phenyl]-prop-1-ynyl}-cyclohex-2-enone (198407-85-1)

Guidance literature:

With tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; copper(l) iodide; trifuran-2-yl-phosphane; triethylamine; In tetrahydrofuran; for 1h; Ambient temperature;

DOI:10.1016/S0040-4039(97)10010-7

Reference yield:

2-iodobenzaldehyde (26260-02-6) → (S)-4-(tert-Butyl-dimethyl-silanyloxy)-2-{3-(tert-butyl-dimethyl-silanyloxy)-3-[2-(3-hydroxy-prop-1-ynyl)-phenyl]-prop-1-ynyl}-cyclohex-2-enone (198407-85-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 86 percent / tetrahydrofuran / 14 h / -60 °C

2: 86 percent / imidazole / CH₂Cl₂ / 12 h / Ambient temperature

3: 74 percent / Pd(PPh₃)2Cl₂, CuI, HN(iPr)2 / tetrahydrofuran / 24 h / Ambient temperature

4: 74 percent / Pd₂dba3*CHCl₃, CuI, NEt₃, tris(2-furyl)phosphine / tetrahydrofuran / 1 h / Ambient temperature

With 1H-imidazole; bis-triphenylphosphine-palladium(II) chloride; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; copper(l) iodide; trifuran-2-yl-phosphane; triethylamine; diisopropylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1016/S0040-4039(97)10010-7

Reference yield:

2-iodobenzyl alcohol (5159-41-1) → (S)-4-(tert-Butyl-dimethyl-silanyloxy)-2-{3-(tert-butyl-dimethyl-silanyloxy)-3-[2-(3-hydroxy-prop-1-ynyl)-phenyl]-prop-1-ynyl}-cyclohex-2-enone (198407-85-1)

Guidance literature:

Multi-step reaction with 5 steps

1: 78 percent / PDC / CH₂Cl₂ / 12 h / Ambient temperature

2: 86 percent / tetrahydrofuran / 14 h / -60 °C

3: 86 percent / imidazole / CH₂Cl₂ / 12 h / Ambient temperature

4: 74 percent / Pd(PPh₃)2Cl₂, CuI, HN(iPr)2 / tetrahydrofuran / 24 h / Ambient temperature

5: 74 percent / Pd₂dba3*CHCl₃, CuI, NEt₃, tris(2-furyl)phosphine / tetrahydrofuran / 1 h / Ambient temperature

With 1H-imidazole; bis-triphenylphosphine-palladium(II) chloride; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; copper(l) iodide; dipyridinium dichromate; trifuran-2-yl-phosphane; triethylamine; diisopropylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1016/S0040-4039(97)10010-7

upstream raw materials:

(4S)-4-[(tert-Butyldimethylsilyl)oxy]-2-iodocyclohex-2-en-1-one

3-{2-[1-(tert-Butyl-dimethyl-silanyloxy)-prop-2-ynyl]-phenyl}-prop-2-yn-1-ol

2-iodobenzaldehyde

2-iodobenzyl alcohol

Downstream raw materials:

(2-{1-(tert-Butyl-dimethyl-silanyloxy)-3-[(S)-3-(tert-butyl-dimethyl-silanyloxy)-6-oxo-cyclohex-1-enyl]-prop-2-ynyl}-phenyl)-propynal