(1S,4S,5R,6S)-7-(4'-methoxyphenylmethoxy-1-methoxy)-4,6-dimethyl-5-(triethylsilyloxy)-1-[3-(2-trimethylsilylethoxymethoxy)phenyl]heptane

Base Information

• Chemical Name: (1S,4S,5R,6S)-7-(4'-methoxyphenylmethoxy-1-methoxy)-4,6-dimethyl-5-(triethylsilyloxy)-1-[3-(2-trimethylsilylethoxymethoxy)phenyl]heptane
• CAS No.: 218152-70-6
• Molecular Formula: C₃₆H₆₂O₆Si₂
• Molecular Weight: 647.056
• Mol file: 218152-70-6.mol

Synonyms:(1S,4S,5R,6S)-7-(4'-methoxyphenylmethoxy-1-methoxy)-4,6-dimethyl-5-(triethylsilyloxy)-1-[3-(2-trimethylsilylethoxymethoxy)phenyl]heptane

Chemical Property of (1S,4S,5R,6S)-7-(4'-methoxyphenylmethoxy-1-methoxy)-4,6-dimethyl-5-(triethylsilyloxy)-1-[3-(2-trimethylsilylethoxymethoxy)phenyl]heptane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,4S,5R,6S)-7-(4'-methoxyphenylmethoxy-1-methoxy)-4,6-dimethyl-5-(triethylsilyloxy)-1-[3-(2-trimethylsilylethoxymethoxy)phenyl]heptane

There total 12 articles about (1S,4S,5R,6S)-7-(4'-methoxyphenylmethoxy-1-methoxy)-4,6-dimethyl-5-(triethylsilyloxy)-1-[3-(2-trimethylsilylethoxymethoxy)phenyl]heptane 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:

3-Hydroxyacetophenone (121-71-1) → (1S,4S,5R,6S)-7-(4'-methoxyphenylmethoxy-1-methoxy)-4,6-dimethyl-5-(triethylsilyloxy)-1-[3-(2-trimethylsilylethoxymethoxy)phenyl]heptane (218152-70-6)

Guidance literature:

Multi-step reaction with 5 steps

1: 79 percent / iPr₂NEt / CH₂Cl₂ / 0 °C

2: 91 percent / 4A MS / benzene / 12 h / Heating

3: 1.) LDA, HMPA / 1.) THF, hexane, 0 deg C, 10 min; -78 deg C, 30 min, 2.) -78 deg C to room temperature, 3 h; room temperature, 7 h

4: 95 percent / BH₃, (R)-C₁₈H₂₀BNO / tetrahydrofuran / 1.5 h / 0 °C

5: 1.) KH / 1.) THF, 0 deg C to room temperature, 1 h, 2.) 0 deg c, 2 h

With N,N,N,N,N,N-hexamethylphosphoric triamide; (R)-C₁₈H₂₀BNO; borane; potassium hydride; N-ethyl-N,N-diisopropylamine; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; benzene;

DOI:10.1021/jo981370x

Reference yield:

O-(4-methoxybenzyl)-trichloroacetimidate (89238-99-3) → (1S,4S,5R,6S)-7-(4'-methoxyphenylmethoxy-1-methoxy)-4,6-dimethyl-5-(triethylsilyloxy)-1-[3-(2-trimethylsilylethoxymethoxy)phenyl]heptane (218152-70-6)

Guidance literature:

Multi-step reaction with 9 steps

1: 67 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 22 h / Ambient temperature

2: DIBAH / CH₂Cl₂ / 1 h / -78 °C

3: 1.) Et₃B, CF₃SO₂H, 2.) iPr₂NEt, 3.) aq. H₂O₂ / 1.) CH₂Cl₂, hexane, 0 deg C, 30 min, 2.) -78 deg C, 3 h; room temperature, 4 h, 3.) MeOH, room temperature, 1 h

4: 98 percent / iPr₂NEt / CH₂Cl₂ / 0.5 h / 0 °C

5: 72 percent / LiBH₄ / ethanol / 2 h / 0 °C

6: 100 percent / PPh₃, imidazole, iPr₂NEt, I₂ / diethyl ether; benzene / 0.5 h

7: 1.) LDA, HMPA / 1.) THF, hexane, 0 deg C, 10 min; -78 deg C, 30 min, 2.) -78 deg C to room temperature, 3 h; room temperature, 7 h

8: 95 percent / BH₃, (R)-C₁₈H₂₀BNO / tetrahydrofuran / 1.5 h / 0 °C

9: 1.) KH / 1.) THF, 0 deg C to room temperature, 1 h, 2.) 0 deg c, 2 h

With 1H-imidazole; N,N,N,N,N,N-hexamethylphosphoric triamide; lithium borohydride; triethyl borane; trifluoromethanesulfinic acid; (R)-C₁₈H₂₀BNO; borane; dihydrogen peroxide; iodine; pyridinium p-toluenesulfonate; potassium hydride; diisobutylaluminium hydride; N-ethyl-N,N-diisopropylamine; triphenylphosphine; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; benzene;

DOI:10.1021/jo981370x

Reference yield:

(2S)-3-[(4-methoxybenzyl)oxy]-2-methylpropanal (132969-60-9) → (1S,4S,5R,6S)-7-(4'-methoxyphenylmethoxy-1-methoxy)-4,6-dimethyl-5-(triethylsilyloxy)-1-[3-(2-trimethylsilylethoxymethoxy)phenyl]heptane (218152-70-6)

Guidance literature:

Multi-step reaction with 7 steps

1: 1.) Et₃B, CF₃SO₂H, 2.) iPr₂NEt, 3.) aq. H₂O₂ / 1.) CH₂Cl₂, hexane, 0 deg C, 30 min, 2.) -78 deg C, 3 h; room temperature, 4 h, 3.) MeOH, room temperature, 1 h

2: 98 percent / iPr₂NEt / CH₂Cl₂ / 0.5 h / 0 °C

3: 72 percent / LiBH₄ / ethanol / 2 h / 0 °C

4: 100 percent / PPh₃, imidazole, iPr₂NEt, I₂ / diethyl ether; benzene / 0.5 h

5: 1.) LDA, HMPA / 1.) THF, hexane, 0 deg C, 10 min; -78 deg C, 30 min, 2.) -78 deg C to room temperature, 3 h; room temperature, 7 h

6: 95 percent / BH₃, (R)-C₁₈H₂₀BNO / tetrahydrofuran / 1.5 h / 0 °C

7: 1.) KH / 1.) THF, 0 deg C to room temperature, 1 h, 2.) 0 deg c, 2 h

With 1H-imidazole; N,N,N,N,N,N-hexamethylphosphoric triamide; lithium borohydride; triethyl borane; trifluoromethanesulfinic acid; (R)-C₁₈H₂₀BNO; borane; dihydrogen peroxide; iodine; potassium hydride; N-ethyl-N,N-diisopropylamine; triphenylphosphine; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; benzene;

DOI:10.1021/jo981370x

upstream raw materials:

3-Hydroxyacetophenone

O-(4-methoxybenzyl)-trichloroacetimidate

(2S)-3-[(4-methoxybenzyl)oxy]-2-methylpropanal

methyl (2S)-[(4-methoxybenzyl)oxy]-2-methylpropanoate