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

Base Information

• Chemical Name: Triethyl-[(E)-(R)-5-(4-methoxy-benzyloxy)-1-((E)-(R)-3-methoxy-1-methyl-allyl)-2-methyl-pent-2-enyloxy]-silane
• CAS No.: 264920-96-9
• Molecular Formula: C₂₅H₄₂O₄Si
• Molecular Weight: 434.692
• Mol file: 264920-96-9.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 6 articles about Triethyl-[(E)-(R)-5-(4-methoxy-benzyloxy)-1-((E)-(R)-3-methoxy-1-methyl-allyl)-2-methyl-pent-2-enyloxy]-silane 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: 97.0%

(methoxymethyl)triphenylphosphonium chloride (4009-98-7) + (E)-(2S,3R)-7-(4-Methoxy-benzyloxy)-2,4-dimethyl-3-triethylsilanyloxy-hept-4-enal (264920-88-9) → Triethyl-[(E)-(R)-5-(4-methoxy-benzyloxy)-1-((E)-(R)-3-methoxy-1-methyl-allyl)-2-methyl-pent-2-enyloxy]-silane (264920-96-9)

Guidance literature:

With potassium tert-butylate; In tetrahydrofuran; at 0 - 22 ℃; for 2h;

DOI:10.1021/ol005510c

Reference yield:

(E)-5-(4-methoxyphenylmethyloxy)-2-methyl-2-pentenal (110597-90-5) → Triethyl-[(E)-(R)-5-(4-methoxy-benzyloxy)-1-((E)-(R)-3-methoxy-1-methyl-allyl)-2-methyl-pent-2-enyloxy]-silane (264920-96-9)

Guidance literature:

Multi-step reaction with 6 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

4: 93 percent / DIBAl-H / CH₂Cl₂ / 0.5 h / -78 °C

5: 99 percent / DMSO; (COCl)2; Et₃N / CH₂Cl₂ / -78 °C

6: 97 percent / KO-t-Bu / tetrahydrofuran / 2 h / 0 - 22 °C

With 2,6-dimethylpyridine; methanol; oxalyl dichloride; di-n-butylboryl trifluoromethanesulfonate; potassium tert-butylate; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; diethyl ether; dichloromethane; 1: Heathcock anti-aldol reaction / 2: methanolysis / 3: silylation / 4: Reduction / 5: Swern oxidation / 6: Wittig reaction;

DOI:10.1021/ol005510c

Reference yield:

(E)-(2S,3R)-3-Hydroxy-7-(4-methoxy-benzyloxy)-2,4-dimethyl-hept-4-enoic acid methyl ester (264920-93-6) → Triethyl-[(E)-(R)-5-(4-methoxy-benzyloxy)-1-((E)-(R)-3-methoxy-1-methyl-allyl)-2-methyl-pent-2-enyloxy]-silane (264920-96-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 90 percent / 2,6-lutidine / CH₂Cl₂ / 0.17 h / -78 °C

2: 93 percent / DIBAl-H / CH₂Cl₂ / 0.5 h / -78 °C

3: 99 percent / DMSO; (COCl)2; Et₃N / CH₂Cl₂ / -78 °C

4: 97 percent / KO-t-Bu / tetrahydrofuran / 2 h / 0 - 22 °C

With 2,6-dimethylpyridine; oxalyl dichloride; potassium tert-butylate; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane; 1: silylation / 2: Reduction / 3: Swern oxidation / 4: Wittig reaction;

DOI:10.1021/ol005510c

upstream raw materials:

(methoxymethyl)triphenylphosphonium chloride

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

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

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

Downstream raw materials:

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

(2R,3R)-5-Methoxy-2-[(E)-4-(4-methoxy-benzyloxy)-1-methyl-but-1-enyl]-3-methyl-tetrahydro-furan

(2R,3R)-5-Allyl-2-[(E)-4-(4-methoxy-benzyloxy)-1-methyl-but-1-enyl]-3-methyl-tetrahydro-furan

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