(1R,5S)-5-(tert-butyldimethylsilyloxy)-1-hydroxy-1-phenyl-3-hexanone

Base Information

• Chemical Name: (1R,5S)-5-(tert-butyldimethylsilyloxy)-1-hydroxy-1-phenyl-3-hexanone
• CAS No.: 474826-38-5
• Molecular Formula: C₁₈H₃₀O₃Si
• Molecular Weight: 322.52
• Mol file: 474826-38-5.mol

Synonyms:(1R,5S)-5-(tert-butyldimethylsilyloxy)-1-hydroxy-1-phenyl-3-hexanone

Chemical Property of (1R,5S)-5-(tert-butyldimethylsilyloxy)-1-hydroxy-1-phenyl-3-hexanone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,5S)-5-(tert-butyldimethylsilyloxy)-1-hydroxy-1-phenyl-3-hexanone

There total 3 articles about (1R,5S)-5-(tert-butyldimethylsilyloxy)-1-hydroxy-1-phenyl-3-hexanone 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: 61.0%

benzaldehyde (100-52-7) + (4S)-4-(tert-butyldimethylsilyloxy)-2-trichlorosilyloxy-1-pentene (474826-26-1) → (1R,5S)-5-(tert-butyldimethylsilyloxy)-1-hydroxy-1-phenyl-3-hexanone (474826-38-5)

Guidance literature:

With chiral phosphoramide catalyst; In dichloromethane; at -78 ℃; for 4h;

DOI:10.1021/jo051930+

Reference yield:

(S)-4-tert-butyldimethylsilyloxy-2-pentanone (474826-06-7) → (1R,5S)-5-(tert-butyldimethylsilyloxy)-1-hydroxy-1-phenyl-3-hexanone (474826-38-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 75 percent / silicon tetrachloride / palladium(II) acetate / CH₂Cl₂ / 0.5 h / 20 °C

2: 61 percent / chiral phosphoramide catalyst / CH₂Cl₂ / 4 h / -78 °C

With tetrachlorosilane; chiral phosphoramide catalyst; palladium diacetate; In dichloromethane; 2: aldol addition;

DOI:10.1021/jo051930+

Reference yield:

benzaldehyde (100-52-7) + (4S)-4-(tert-butyldimethylsilyloxy)-2-trichlorosilyloxy-1-pentene (474826-26-1) → (1S,5S)-5-(tert-butyldimethylsilyloxy)-1-hydroxy-1-phenyl-3-hexanone + (1R,5S)-5-(tert-butyldimethylsilyloxy)-1-hydroxy-1-phenyl-3-hexanone (474826-38-5)

Guidance literature:

With (4S,5S)-1,3-dimethyl-4,5-diphenyl-2-(1-piperidinyl)-1,3,2-diazaphospholidine 2-oxide; In dichloromethane; at -78 ℃; for 4h; Further Variations:; Catalysts; Product distribution;

DOI:10.1021/ol026594n

upstream raw materials:

benzaldehyde

(4S)-4-(tert-butyldimethylsilyloxy)-2-trichlorosilyloxy-1-pentene

(S)-4-tert-butyldimethylsilyloxy-2-pentanone