(R)-(E)-1-<(tert-Butyldimethylsilyl)oxy>-2-<<<(p-methoxybenzyl)oxy>methoxy>methyl>-5-methylhex-3-ene

Base Information

• Chemical Name: (R)-(E)-1-<(tert-Butyldimethylsilyl)oxy>-2-<<<(p-methoxybenzyl)oxy>methoxy>methyl>-5-methylhex-3-ene
• CAS No.: 138436-23-4
• Molecular Formula: C₂₃H₄₀O₄Si
• Molecular Weight: 408.654
• Mol file: 138436-23-4.mol

Synonyms:(R)-(E)-1-<(tert-Butyldimethylsilyl)oxy>-2-<<<(p-methoxybenzyl)oxy>methoxy>methyl>-5-methylhex-3-ene

Chemical Property of (R)-(E)-1-<(tert-Butyldimethylsilyl)oxy>-2-<<<(p-methoxybenzyl)oxy>methoxy>methyl>-5-methylhex-3-ene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-(E)-1-<(tert-Butyldimethylsilyl)oxy>-2-<<<(p-methoxybenzyl)oxy>methoxy>methyl>-5-methylhex-3-ene

There total 13 articles about (R)-(E)-1-<(tert-Butyldimethylsilyl)oxy>-2-<<<(p-methoxybenzyl)oxy>methoxy>methyl>-5-methylhex-3-ene 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: 85.0%

(R)-(E)-2-<<(tert-Butyldimethylsilyl)oxy>methyl>-5-methylhex-3-en-1-ol (138513-53-8) + para-methoxybenzyl chloride (88023-78-3) → (R)-(E)-1-<(tert-Butyldimethylsilyl)oxy>-2-<<<(p-methoxybenzyl)oxy>methoxy>methyl>-5-methylhex-3-ene (138436-23-4)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In dichloromethane; a.) 0 deg C, b.) room temperature;

DOI:10.1021/jo00031a039

Reference yield:

(2R,3E)-2-(hydroxymethyl)-5-methylhex-3-enyl acetate (155489-75-1) → (R)-(E)-1-<(tert-Butyldimethylsilyl)oxy>-2-<<<(p-methoxybenzyl)oxy>methoxy>methyl>-5-methylhex-3-ene (138436-23-4)

Guidance literature:

Multi-step reaction with 3 steps

1: EtN(iPr)2 / CH₂Cl₂

2: KOH / methanol

3: imidazole / dimethylformamide

With 1H-imidazole; potassium hydroxide; N-ethyl-N,N-diisopropylamine; In methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(00)73162-5

Reference yield:

diethyl (E)-2-(3-methyl-1-butene-1-yl)malonate (138435-98-0) → (R)-(E)-1-<(tert-Butyldimethylsilyl)oxy>-2-<<<(p-methoxybenzyl)oxy>methoxy>methyl>-5-methylhex-3-ene (138436-23-4)

Guidance literature:

Multi-step reaction with 5 steps

1: 17.20 g / LiAlH₄ / diethyl ether / a.) 0 deg C, 30 min, b.) room temperature, 5.5 h

2: 72 percent / pyridine / 4 h / 0 °C

3: 75 percent / H₂O; propan-2-ol / pig pancreatic lipase, pH 7 buffer (K₂HPO₄-KH₂PO₄)

4: 1.) imidazole, 2.) KOH / 1.) DMF, room temperature, 2.5 h, 2.) MeOH, a.) 0 deg C, 2 h, b.) room temperature, 1 h

5: 85 percent / EtN(iPr)2 / CH₂Cl₂ / a.) 0 deg C, b.) room temperature

With pyridine; 1H-imidazole; potassium hydroxide; lithium aluminium tetrahydride; N-ethyl-N,N-diisopropylamine; In diethyl ether; dichloromethane; water; isopropyl alcohol;

DOI:10.1021/jo00031a039

upstream raw materials:

(R)-(E)-2-<<(tert-Butyldimethylsilyl)oxy>methyl>-5-methylhex-3-en-1-ol

para-methoxybenzyl chloride

tert-butyldimethylsilyl chloride

(2R,3E)-2-(hydroxymethyl)-5-methylhex-3-enyl acetate

Downstream raw materials:

(2R,3R)-4-<<(t-butyldimethyl)silyl>oxy>-3-<<<(p-methoxybenzyl)oxy>methoxy>methyl>-2-butanol

(2S,3R)-2-<<<(p-methoxybenzyl)oxy>methoxy>methyl>-3-<(tri-i-propylsilyl)oxy>butan-1-ol

(2R,3R)-1-<<(t-butyldimethyl)silyl>oxy>-2-<<<(p-methoxybenzyl)oxy>methoxy>methyl>-3-<(tri-i-propylsilyl)oxy>butane

(2S,3R)-N-Benzyloxy-2-(4-methoxy-benzyloxymethoxymethyl)-3-triisopropylsilanyloxy-butyramide