(2S,3S)-6-(tert-Butyl-dimethyl-silanyloxy)-3-hydroxy-2-methyl-4-methylene-1-phenyl-hexan-1-one

Base Information

• Chemical Name: (2S,3S)-6-(tert-Butyl-dimethyl-silanyloxy)-3-hydroxy-2-methyl-4-methylene-1-phenyl-hexan-1-one
• CAS No.: 159734-11-9
• Molecular Formula: C₂₀H₃₂O₃Si
• Molecular Weight: 348.558
• Mol file: 159734-11-9.mol

Synonyms:(2S,3S)-6-(tert-Butyl-dimethyl-silanyloxy)-3-hydroxy-2-methyl-4-methylene-1-phenyl-hexan-1-one

Chemical Property of (2S,3S)-6-(tert-Butyl-dimethyl-silanyloxy)-3-hydroxy-2-methyl-4-methylene-1-phenyl-hexan-1-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S)-6-(tert-Butyl-dimethyl-silanyloxy)-3-hydroxy-2-methyl-4-methylene-1-phenyl-hexan-1-one

There total 6 articles about (2S,3S)-6-(tert-Butyl-dimethyl-silanyloxy)-3-hydroxy-2-methyl-4-methylene-1-phenyl-hexan-1-one 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%

phenylmagnesium chloride (100-59-4) + (2S,3S)-6-(tert-Butyl-dimethyl-silanyloxy)-3-hydroxy-2-methyl-4-methylene-hexanoic acid methoxy-methyl-amide (159734-10-8) → (2S,3S)-6-(tert-Butyl-dimethyl-silanyloxy)-3-hydroxy-2-methyl-4-methylene-1-phenyl-hexan-1-one (159734-11-9)

Guidance literature:

In tetrahydrofuran; for 16h; -78 deg C to rt;

DOI:10.1016/0040-4039(94)88298-3

Reference yield:

4-(tert-butyldimethylsilanyloxy)butanal (87184-81-4) → (2S,3S)-6-(tert-Butyl-dimethyl-silanyloxy)-3-hydroxy-2-methyl-4-methylene-1-phenyl-hexan-1-one (159734-11-9)

Guidance literature:

Multi-step reaction with 4 steps

1: CH₂Cl₂ / Ambient temperature

2: 70 percent / n-Bu₂BOTf, iPr₂NEt / CH₂Cl₂ / 1.) -78 deg C, 30 min, 2.) 0 deg C, 1 h

3: 86 percent / AlMe₃ / CH₂Cl₂; toluene / 1.) r.t., 30 min, 2.) 0 deg C, 3.5 h

4: 74 percent / tetrahydrofuran / 16 h / Ambient temperature

With di-n-butylboryl trifluoromethanesulfonate; trimethylaluminum; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; toluene;

Reference yield:

4-tert-butyldimethylsilyloxybutan-1-ol (87184-99-4) → (2S,3S)-6-(tert-Butyl-dimethyl-silanyloxy)-3-hydroxy-2-methyl-4-methylene-1-phenyl-hexan-1-one (159734-11-9)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) DMSO, (COCl)2, 2.) Et₃N / 1.) CH₂Cl₂, -70 deg C, 15 min, 2.) CH₂Cl₂, r.t., 15 min

2: CH₂Cl₂ / Ambient temperature

3: 70 percent / n-Bu₂BOTf, iPr₂NEt / CH₂Cl₂ / 1.) -78 deg C, 30 min, 2.) 0 deg C, 1 h

4: 86 percent / AlMe₃ / CH₂Cl₂; toluene / 1.) r.t., 30 min, 2.) 0 deg C, 3.5 h

5: 74 percent / tetrahydrofuran / 16 h / Ambient temperature

With oxalyl dichloride; di-n-butylboryl trifluoromethanesulfonate; trimethylaluminum; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; toluene;

upstream raw materials:

phenylmagnesium chloride

(2S,3S)-6-(tert-Butyl-dimethyl-silanyloxy)-3-hydroxy-2-methyl-4-methylene-hexanoic acid methoxy-methyl-amide

4-(tert-butyldimethylsilanyloxy)butanal

4-tert-butyldimethylsilyloxybutan-1-ol

Downstream raw materials:

(2R,3S)-6-(tert-Butyl-dimethyl-silanyloxy)-2-methyl-4-methylene-1-phenyl-hexan-3-ol

tert-Butyl-dimethyl-[3-((4S,5S)-2,2,5-trimethyl-6-phenyl-[1,3]dioxan-4-yl)-but-3-enyloxy]-silane

(-)-(1'S,2'R)-3-(1'-Benzyloxy-2'-methyl-3'-phenylpropyl)but-3-en-1-ol

3-((4S,5S,6S)-2,2,5-Trimethyl-6-phenyl-[1,3]dioxan-4-yl)-but-3-en-1-ol