(E)-(2S,3R)-7-(4-Methoxy-benzyloxy)-2,4-dimethyl-3-triethylsilanyloxy-hept-4-enoic acid methyl ester

Base Information

• Chemical Name: (E)-(2S,3R)-7-(4-Methoxy-benzyloxy)-2,4-dimethyl-3-triethylsilanyloxy-hept-4-enoic acid methyl ester
• CAS No.: 264920-94-7
• Molecular Formula: C₂₄H₄₀O₅Si
• Molecular Weight: 436.664
• Mol file: 264920-94-7.mol

Synonyms:(E)-(2S,3R)-7-(4-Methoxy-benzyloxy)-2,4-dimethyl-3-triethylsilanyloxy-hept-4-enoic acid methyl ester

Chemical Property of (E)-(2S,3R)-7-(4-Methoxy-benzyloxy)-2,4-dimethyl-3-triethylsilanyloxy-hept-4-enoic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-(2S,3R)-7-(4-Methoxy-benzyloxy)-2,4-dimethyl-3-triethylsilanyloxy-hept-4-enoic acid methyl ester

There total 3 articles about (E)-(2S,3R)-7-(4-Methoxy-benzyloxy)-2,4-dimethyl-3-triethylsilanyloxy-hept-4-enoic acid methyl ester 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%

triethylsilyl trifluoromethyl sulfonate (79271-56-0) + (E)-(2S,3R)-3-Hydroxy-7-(4-methoxy-benzyloxy)-2,4-dimethyl-hept-4-enoic acid methyl ester (264920-93-6) → (E)-(2S,3R)-7-(4-Methoxy-benzyloxy)-2,4-dimethyl-3-triethylsilanyloxy-hept-4-enoic acid methyl ester (264920-94-7)

Guidance literature:

With 2,6-dimethylpyridine; In dichloromethane; at -78 ℃; for 0.166667h;

DOI:10.1021/ol005510c

Reference yield:

(E)-5-(4-methoxyphenylmethyloxy)-2-methyl-2-pentenal (110597-90-5) → (E)-(2S,3R)-7-(4-Methoxy-benzyloxy)-2,4-dimethyl-3-triethylsilanyloxy-hept-4-enoic acid methyl ester (264920-94-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 68 percent / Bu₂BOTf; i-Pr₂NEt / diethyl ether / 6 h / -78 °C

2: 80 percent / MeOH / 2 h / -78 - -10 °C

3: 90 percent / 2,6-lutidine / CH₂Cl₂ / 0.17 h / -78 °C

With 2,6-dimethylpyridine; methanol; di-n-butylboryl trifluoromethanesulfonate; N-ethyl-N,N-diisopropylamine; In diethyl ether; dichloromethane; 1: Heathcock anti-aldol reaction / 2: methanolysis / 3: silylation;

DOI:10.1021/ol005510c

Reference yield:

(4R,5S)-3-[(E)-(2S,3R)-3-Hydroxy-7-(4-methoxy-benzyloxy)-2,4-dimethyl-hept-4-enoyl]-4-methyl-5-phenyl-oxazolidin-2-one (264920-92-5) → (E)-(2S,3R)-7-(4-Methoxy-benzyloxy)-2,4-dimethyl-3-triethylsilanyloxy-hept-4-enoic acid methyl ester (264920-94-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 80 percent / MeOH / 2 h / -78 - -10 °C

2: 90 percent / 2,6-lutidine / CH₂Cl₂ / 0.17 h / -78 °C

With 2,6-dimethylpyridine; methanol; In dichloromethane; 1: methanolysis / 2: silylation;

DOI:10.1021/ol005510c

upstream raw materials:

triethylsilyl trifluoromethyl sulfonate

(E)-(2S,3R)-3-Hydroxy-7-(4-methoxy-benzyloxy)-2,4-dimethyl-hept-4-enoic acid methyl ester

(E)-5-(4-methoxyphenylmethyloxy)-2-methyl-2-pentenal

(4R,5S)-3-[(E)-(2S,3R)-3-Hydroxy-7-(4-methoxy-benzyloxy)-2,4-dimethyl-hept-4-enoyl]-4-methyl-5-phenyl-oxazolidin-2-one

Downstream raw materials:

Triethyl-[(E)-(R)-5-(4-methoxy-benzyloxy)-1-((E)-(R)-3-methoxy-1-methyl-allyl)-2-methyl-pent-2-enyloxy]-silane

(E)-(2S,3R)-7-(4-Methoxy-benzyloxy)-2,4-dimethyl-3-triethylsilanyloxy-hept-4-enal

3-{(4R,5R)-5-[(E)-4-(4-Methoxy-benzyloxy)-1-methyl-but-1-enyl]-4-methyl-tetrahydro-furan-2-yl}-propan-1-ol

Acetic acid (4R,5R)-5-[(E)-4-(4-methoxy-benzyloxy)-1-methyl-but-1-enyl]-4-methyl-tetrahydro-furan-2-yl ester