ethyl (2S)-2-<(t-butyldimethylsilyl)oxy>-4-<(4-methoxybenzyloxy)methyl>-5-methyl-4-hexenoate

Base Information

• Chemical Name: ethyl (2S)-2-<(t-butyldimethylsilyl)oxy>-4-<(4-methoxybenzyloxy)methyl>-5-methyl-4-hexenoate
• CAS No.: 148675-59-6
• Molecular Formula: C₂₄H₄₀O₅Si
• Molecular Weight: 436.664
• Mol file: 148675-59-6.mol

Synonyms:ethyl (2S)-2-<(t-butyldimethylsilyl)oxy>-4-<(4-methoxybenzyloxy)methyl>-5-methyl-4-hexenoate

Chemical Property of ethyl (2S)-2-<(t-butyldimethylsilyl)oxy>-4-<(4-methoxybenzyloxy)methyl>-5-methyl-4-hexenoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl (2S)-2-<(t-butyldimethylsilyl)oxy>-4-<(4-methoxybenzyloxy)methyl>-5-methyl-4-hexenoate

There total 6 articles about ethyl (2S)-2-<(t-butyldimethylsilyl)oxy>-4-<(4-methoxybenzyloxy)methyl>-5-methyl-4-hexenoate 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: 95.0%

tert-butyldimethylsilyl chloride (18162-48-6) + ethyl 2-hydroxy-4-<(4-methoxybenzyloxy)methyl>-5-methyl-4-hexenoate (148763-52-4) → ethyl (2S)-2-<(t-butyldimethylsilyl)oxy>-4-<(4-methoxybenzyloxy)methyl>-5-methyl-4-hexenoate (148675-59-6)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(01)86347-X

Reference yield:

2-isopropylallyl alcohol (26903-66-2) → ethyl (2S)-2-<(t-butyldimethylsilyl)oxy>-4-<(4-methoxybenzyloxy)methyl>-5-methyl-4-hexenoate (148675-59-6)

Guidance literature:

Multi-step reaction with 5 steps

1: 1) NaH / 1) THF, DMF, 0 deg C, 30 min, 2) THF, 120 min

2: SnCl₄ / CH₂Cl₂ / 0.08 h / -78 °C

3: 1M aq. NaOH / methanol; tetrahydrofuran / 5 h / Heating

4: DBU / benzene / 5 h / Heating

5: 95 percent / imidazole / dimethylformamide

With 1H-imidazole; sodium hydroxide; tin(IV) chloride; sodium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; benzene;

DOI:10.1016/S0040-4020(01)86347-X

Reference yield:

1-(4-methoxybenzyloxy)-2-(2-propyl)-2-propene (148675-55-2) → ethyl (2S)-2-<(t-butyldimethylsilyl)oxy>-4-<(4-methoxybenzyloxy)methyl>-5-methyl-4-hexenoate (148675-59-6)

Guidance literature:

Multi-step reaction with 4 steps

1: SnCl₄ / CH₂Cl₂ / 0.08 h / -78 °C

2: 1M aq. NaOH / methanol; tetrahydrofuran / 5 h / Heating

3: DBU / benzene / 5 h / Heating

4: 95 percent / imidazole / dimethylformamide

With 1H-imidazole; sodium hydroxide; tin(IV) chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; benzene;

DOI:10.1016/S0040-4020(01)86347-X

upstream raw materials:

tert-butyldimethylsilyl chloride

ethyl 2-hydroxy-4-<(4-methoxybenzyloxy)methyl>-5-methyl-4-hexenoate

2-isopropylallyl alcohol

1-(4-methoxybenzyloxy)-2-(2-propyl)-2-propene

Downstream raw materials:

ethyl (4S)-(2Z)-4-<(t-butyldimethylsilyl)oxy>-3-<(diethylphosphoryl)oxy>-6-<(4-methoxybenzyloxy)methyl>-7-methyl-2,6-octadienoate

ethyl (4S)-(2Z)-4-<(t-butyldimethylsilyl)oxy>-6-<(4-methoxybenzyloxy)methyl>-7-methyl-3-<(trimethylsilyl)methyl>-2,6-octadienoate