(-)-3-(2-((2R,4S)-2-(2-(tert-butyldiphenylsilyloxy)ethyl)-4-(triisopropylsilyloxy)-3,4-dihydro-2H-pyran-6-yl)-5-(trifluoromethyl)phenyl)propan-1-ol

Base Information

• Chemical Name: (-)-3-(2-((2R,4S)-2-(2-(tert-butyldiphenylsilyloxy)ethyl)-4-(triisopropylsilyloxy)-3,4-dihydro-2H-pyran-6-yl)-5-(trifluoromethyl)phenyl)propan-1-ol
• CAS No.: 1308314-57-9
• Molecular Formula: C₄₂H₅₉F₃O₄Si₂
• Molecular Weight: 741.094

Synonyms:

Chemical Property of (-)-3-(2-((2R,4S)-2-(2-(tert-butyldiphenylsilyloxy)ethyl)-4-(triisopropylsilyloxy)-3,4-dihydro-2H-pyran-6-yl)-5-(trifluoromethyl)phenyl)propan-1-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (-)-3-(2-((2R,4S)-2-(2-(tert-butyldiphenylsilyloxy)ethyl)-4-(triisopropylsilyloxy)-3,4-dihydro-2H-pyran-6-yl)-5-(trifluoromethyl)phenyl)propan-1-ol

There total 7 articles about (-)-3-(2-((2R,4S)-2-(2-(tert-butyldiphenylsilyloxy)ethyl)-4-(triisopropylsilyloxy)-3,4-dihydro-2H-pyran-6-yl)-5-(trifluoromethyl)phenyl)propan-1-ol 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:

(2-bromo-5-(trifluoromethyl)phenyl)methanol (869725-53-1) → (-)-3-(2-((2R,4S)-2-(2-(tert-butyldiphenylsilyloxy)ethyl)-4-(triisopropylsilyloxy)-3,4-dihydro-2H-pyran-6-yl)-5-(trifluoromethyl)phenyl)propan-1-ol (1308314-57-9)

Guidance literature:

Multi-step reaction with 7 steps

1.1: Dess-Martin periodane / dichloromethane / 1 h / 20 °C / Inert atmosphere

2.1: sodium hydride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere

2.2: 0 - 20 °C / Inert atmosphere

3.1: sodium acetate; toluene-4-sulfonic acid hydrazide / tetrahydrofuran; water / 20 h / Reflux; Inert atmosphere

4.1: diisobutylaluminium hydride / toluene / -78 - 20 °C / Inert atmosphere

5.1: dmap; triethylamine / dichloromethane / 2 h / 20 °C / Inert atmosphere

6.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾ / toluene / Reflux; Darkness; Inert atmosphere

7.1: methanol; potassium carbonate / tetrahydrofuran

With methanol; dmap; tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium acetate; sodium hydride; diisobutylaluminium hydride; potassium carbonate; Dess-Martin periodane; triethylamine; toluene-4-sulfonic acid hydrazide; In tetrahydrofuran; dichloromethane; water; toluene; 2.1: Horner-Wadsworth-Emmons olefination / 2.2: Horner-Wadsworth-Emmons olefination / 6.1: Stille coupling;

DOI:10.1021/ja201249c

Reference yield:

ethyl 3-(2-bromo-5-(trifluoromethyl)phenyl)propanoate (1261779-31-0) → (-)-3-(2-((2R,4S)-2-(2-(tert-butyldiphenylsilyloxy)ethyl)-4-(triisopropylsilyloxy)-3,4-dihydro-2H-pyran-6-yl)-5-(trifluoromethyl)phenyl)propan-1-ol (1308314-57-9)

Guidance literature:

Multi-step reaction with 4 steps

1: diisobutylaluminium hydride / toluene / -78 - 20 °C / Inert atmosphere

2: dmap; triethylamine / dichloromethane / 2 h / 20 °C / Inert atmosphere

3: tetrakis(triphenylphosphine) palladium⁽⁰⁾ / toluene / Reflux; Darkness; Inert atmosphere

4: methanol; potassium carbonate / tetrahydrofuran

With methanol; dmap; tetrakis(triphenylphosphine) palladium⁽⁰⁾; diisobutylaluminium hydride; potassium carbonate; triethylamine; In tetrahydrofuran; dichloromethane; toluene; 3: Stille coupling;

DOI:10.1021/ja201249c

Reference yield:

3-(2-bromo-5-(trifluoromethyl)phenyl)propyl acetate → (-)-3-(2-((2R,4S)-2-(2-(tert-butyldiphenylsilyloxy)ethyl)-4-(triisopropylsilyloxy)-3,4-dihydro-2H-pyran-6-yl)-5-(trifluoromethyl)phenyl)propan-1-ol (1308314-57-9)

Guidance literature:

Multi-step reaction with 2 steps

1: tetrakis(triphenylphosphine) palladium⁽⁰⁾ / toluene / Reflux; Darkness; Inert atmosphere

2: methanol; potassium carbonate / tetrahydrofuran

With methanol; tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate; In tetrahydrofuran; toluene; 1: Stille coupling;

DOI:10.1021/ja201249c

upstream raw materials:

(2-bromo-5-(trifluoromethyl)phenyl)methanol

ethyl 3-(2-bromo-5-(trifluoromethyl)phenyl)propanoate

2-bromo-5-(trifluoromethyl)benzaldehyde

Downstream raw materials:

(+)-(1R,3'R,4'S_.6'R)-6'-(2-(tert-butyldiphenylsilyloxy)ethyl)-7-(trifluoromethyl)-4'-(triisopropylsilyloxy)-3',4',5',6'-tetrahydro-3H-spiro[benzo[c]oxepine-1,2'-pyran]-3'-ol

(+)-(1S,3'R,4'S_.6'R)-6'-(2-(tert-butyldiphenylsilyloxy)ethyl)-7-(trifluoromethyl)-4'-(triisopropylsilyloxy)-3',4',5',6'-tetrahydro-3H-spiro[benzo[c]oxepine-1,2'-pyran]-3'-ol

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