(+)-(2S,4R,5R)-5-hydroxy-4-methyl-5-phenyl-2-[((dimethyl)-(1,1-dimethylethyl)silyl)oxy]-3-pentanone

Base Information

• Chemical Name: (+)-(2S,4R,5R)-5-hydroxy-4-methyl-5-phenyl-2-[((dimethyl)-(1,1-dimethylethyl)silyl)oxy]-3-pentanone
• CAS No.: 188677-78-3
• Molecular Formula: C₁₈H₃₀O₃Si
• Molecular Weight: 322.52
• Mol file: 188677-78-3.mol

Synonyms:(+)-(2S,4R,5R)-5-hydroxy-4-methyl-5-phenyl-2-[((dimethyl)-(1,1-dimethylethyl)silyl)oxy]-3-pentanone

Chemical Property of (+)-(2S,4R,5R)-5-hydroxy-4-methyl-5-phenyl-2-[((dimethyl)-(1,1-dimethylethyl)silyl)oxy]-3-pentanone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+)-(2S,4R,5R)-5-hydroxy-4-methyl-5-phenyl-2-[((dimethyl)-(1,1-dimethylethyl)silyl)oxy]-3-pentanone

There total 9 articles about (+)-(2S,4R,5R)-5-hydroxy-4-methyl-5-phenyl-2-[((dimethyl)-(1,1-dimethylethyl)silyl)oxy]-3-pentanone 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: 90.0%

benzaldehyde (100-52-7) + (S) 4-(tert-butyldimethylsilyloxy)-3-pentanone (187590-50-7) → (+)-(2S,4R,5R)-5-hydroxy-4-methyl-5-phenyl-2-[((dimethyl)-(1,1-dimethylethyl)silyl)oxy]-3-pentanone (188677-78-3)

Guidance literature:

With titanium tetrachloride; N-ethyl-N,N-diisopropylamine; 1.) -78 deg C, 1.5 h; 2.) -78 deg C, 2 h;

DOI:10.1016/S0040-4039(97)00108-1

Reference yield: 82.0%

benzaldehyde (100-52-7) + (S) 4-(tert-butyldimethylsilyloxy)-3-pentanone (187590-50-7) → (+)-(2S,4R,5R)-5-hydroxy-4-methyl-5-phenyl-2-[((dimethyl)-(1,1-dimethylethyl)silyl)oxy]-3-pentanone (188677-78-3) + (2S,4S,5S)-5-hydroxy-4-methyl-5-phenyl-2-[((dimethyl)-(1,1-dimethylethyl)silyl)oxy]-3-pentanone

Guidance literature:

With titanium tetrachloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; at -78 ℃; for 0.5h;

DOI:10.1016/j.tet.2006.09.034

Reference yield:

benzaldehyde (100-52-7) + (-)-(S)-(Z)-trimethyl[(1-((1-((dimethyl)-(1,1-dimethylethyl)silyl)oxy)ethyl)propenyl)oxy]silane (354116-87-3) → (+)-(2S,4R,5R)-5-hydroxy-4-methyl-5-phenyl-2-[((dimethyl)-(1,1-dimethylethyl)silyl)oxy]-3-pentanone (188677-78-3) + 4-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-2-methyl-1-phenyl-pentan-3-one

Guidance literature:

(-)-(S)-(Z)-trimethyl[(1-((1-((dimethyl)-(1,1-dimethylethyl)silyl)oxy)ethyl)propenyl)oxy]silane; With mercury(II) diacetate; In dichloromethane; at 20 ℃; for 18h;

benzaldehyde; With N,N,N,N,N,N-hexamethylphosphoric triamide; In dichloromethane; at -78 ℃; for 10h; Further stages.;

DOI:10.1021/ol0160497

upstream raw materials:

benzaldehyde

(S) 4-(tert-butyldimethylsilyloxy)-3-pentanone

(-)-(S)-(Z)-trimethyl[(1-((1-((dimethyl)-(1,1-dimethylethyl)silyl)oxy)ethyl)propenyl)oxy]silane

(S)-(Z)-trichloro[(1-((1-((dimethyl)-(1,1-dimethylethyl)silyl)oxy)ethyl)propenyl)oxy]silane

Downstream raw materials:

(1R,2R,4S)-1,4-dihydroxy-2-methyl-1-phenyl-3-pentanone

(2R,3R)-(+)-3-hydroxy-2-methyl-3-phenylpropanoic acid